blc-org/A-secret-data-repo huggingface dataset:
Task: reaction
rxn_cls: CO2H-tBu deprotection
reactants: Cl
Cl
CC(C)(C)OC(=O)c1ccc(CC(=O)NCc2ccc(C(=O)Oc3ccc4cc(C(=N)N)ccc4c3)o2)cc1
reagents: O
CC(=O)O
rxn_smiles: Cl.Cl.CC(C)(C)OC(=O)c1ccc(CC(=O)NCc2ccc(C(=O)Oc3ccc4cc(C(=N)N)ccc4c3)o2)cc1>O.CC(=O)O>Cl.N=C(N)c1ccc2cc(OC(=O)c3ccc(CNC(=O)Cc4ccc(C(=O)O)cc4)o3)ccc2c1
Answer: Major Product: ClN=C(N)c1ccc2cc(OC(=O)c3ccc(CNC(=O)Cc4ccc(C(=O)O)cc4)o3)ccc2c1
Byproduct(s): CC(C)(C)O
Task: reaction
rxn_cls: Triflyloxy Sonogashira coupling
reactants: COC(=O)C(OC)Oc1ccc2ccc(OS(=O)(=O)C(F)(F)F)cc2c1
C#C[Si](C)(C)C
reagents: Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
CCN(CC)CC
C1CCOC1
N#N
[Cu]I
rxn_smiles: COC(=O)C(OC)Oc1ccc2ccc(OS(=O)(=O)C(F)(F)F)cc2c1.C#C[Si](C)(C)C>Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.CCN(CC)CC.C1CCOC1.N#N.[Cu]I>COC(=O)C(OC)Oc1ccc2ccc(C#C[Si](C)(C)C)cc2c1
Answer: Major Product: COC(=O)C(OC)Oc1ccc2ccc(C#C[Si](C)(C)C)cc2c1
Byproduct(s): COC(=O)C(OC)Oc1ccc2ccc(OS(=O)(=O)C(F)(F)C#C[Si](C)(C)C)cc2c1Cl[Cu]F[Cu]IO=S(=O)(O[Pd](Cl)P(c1ccccc1)(c1ccccc1)c1ccccc1)C(F)(F)Fc1ccc(P(c2ccccc2)c2ccccc2)cc1
Task: reaction
rxn_cls: CO2H-Me deprotection
reactants: CCCC(C(=O)OC)C(c1ccccc1)c1ccc2c(cnn2-c2ccc(F)cc2)c1
reagents: CO
CS(C)=O
O[Na]
rxn_smiles: CCCC(C(=O)OC)C(c1ccccc1)c1ccc2c(cnn2-c2ccc(F)cc2)c1>CO.CS(C)=O.O[Na]>CCCC(C(=O)O)C(c1ccccc1)c1ccc2c(cnn2-c2ccc(F)cc2)c1
Answer: Major Product: CCCC(C(=O)O)C(c1ccccc1)c1ccc2c(cnn2-c2ccc(F)cc2)c1
Byproduct(s): CO[Na+]
Task: reaction
rxn_cls: Grignard + acid chloride ketone synthesis
reactants: CCC(C)CC(=O)Cl
CC(C)(C)[Mg]Cl
reagents: CCCC(=O)C(C)(C)CC
CCOCC
Cl[Cu]
rxn_smiles: CCC(C)CC(=O)Cl.CC(C)(C)[Mg]Cl>CCCC(=O)C(C)(C)CC.CCOCC.Cl[Cu]>CCC(C)CC(=O)C(C)(C)C
Answer: Major Product: CCC(C)CC(=O)C(C)(C)C
Byproduct(s): [Cl-][Mg+]Cl
Task: reaction
rxn_cls: Friedel-Crafts acylation
reactants: CC(Cl)C(=O)Cl
Fc1cccc(F)c1
reagents: O
Cl
ClCCCl
Cl[Al](Cl)Cl
rxn_smiles: CC(Cl)C(=O)Cl.Fc1cccc(F)c1>O.Cl.ClCCCl.Cl[Al](Cl)Cl>CC(Cl)C(=O)c1ccc(F)cc1F
Answer: Major Product: CC(Cl)C(=O)c1ccc(F)cc1F
Byproduct(s): CC(Cl)C(=O)c1c(F)cccc1FCC(Cl)C(=O)c1cc(F)cc(F)c1Cl
Task: reaction
rxn_cls: Bromo Grignard reaction
reactants: CCOC(=O)C(=O)C(F)(F)F
Cc1cc(Br)cc([Mg]Br)c1
rxn_smiles: CCOC(=O)C(=O)C(F)(F)F.Cc1cc(Br)cc([Mg]Br)c1>>CCOC(=O)C(O)(c1cc(C)cc(Br)c1)C(F)(F)F
Answer: Major Product: CCOC(=O)C(O)(c1cc(C)cc(Br)c1)C(F)(F)F
Byproduct(s): Cc1c[c-]cc(Br)c1[Mg+]Br
Task: reaction
rxn_cls: Pinner reaction
reactants: COc1cc2nc(N3CCN(C#N)CC3)nc(N)c2cc1OC
CO
reagents: Nc1c(/N=N/c2ccc(-c3ccc(/N=N/c4cc(S(=O)(=O)O)c5ccccc5c4N)cc3)cc2)cc(S(=O)(=O)O)c2ccccc12
CCOCC
O[Na]
Cl
rxn_smiles: COc1cc2nc(N3CCN(C#N)CC3)nc(N)c2cc1OC.CO>Nc1c(/N=N/c2ccc(-c3ccc(/N=N/c4cc(S(=O)(=O)O)c5ccccc5c4N)cc3)cc2)cc(S(=O)(=O)O)c2ccccc12.CCOCC.O[Na].Cl>COC(=N)N1CCN(c2nc(N)c3cc(OC)c(OC)cc3n2)CC1
Answer: {"Major Product": "COC(=N)N1CCN(c2nc(N)c3cc(OC)c(OC)cc3n2)CC1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Sulfanyl to sulfonyl
reactants: CC(C)SCC1CN(C(=O)OC(C)(C)C)C1
reagents: O=S(=O)(O[K])OO[K]
O=S(=O)(O[K])OO[K]
O=S(=O)(O)O[K]
O=S(O[Na])O[Na]
O=S(=O)(O)O
rxn_smiles: CC(C)SCC1CN(C(=O)OC(C)(C)C)C1>O=S(=O)(O[K])OO[K].O=S(=O)(O[K])OO[K].O=S(=O)(O)O[K].O=S(O[Na])O[Na].O=S(=O)(O)O>CC(C)S(=O)(=O)CC1CN(C(=O)OC(C)(C)C)C1
Answer: Major Product: CC(C)S(=O)(=O)CC1CN(C(=O)OC(C)(C)C)C1
Byproduct(s): OS(=O)(=O)O[K]OS(=O)(=O)O[K][K+][K+]
Task: reaction
rxn_cls: Ester Schotten-Baumann
reactants: Oc1ccc(OCc2ccccc2)cc1
CC(C)C(=O)Cl
reagents: c1ccncc1
c1ccncc1
CCOCC
O[K]
O
Cl
rxn_smiles: Oc1ccc(OCc2ccccc2)cc1.CC(C)C(=O)Cl>c1ccncc1.c1ccncc1.CCOCC.O[K].O.Cl>CC(C)C(=O)Oc1ccc(OCc2ccccc2)cc1
Answer: Major Product: CC(C)C(=O)Oc1ccc(OCc2ccccc2)cc1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Weinreb ketone synthesis
reactants: CON(C)C(=O)Cc1ccc(Cl)cc1Cl
C[Mg]Br
reagents: Cc1ccccc1
C1CCOC1
C1CCOC1
rxn_smiles: CON(C)C(=O)Cc1ccc(Cl)cc1Cl.C[Mg]Br>Cc1ccccc1.C1CCOC1.C1CCOC1>CC(=O)Cc1ccc(Cl)cc1Cl
Answer: Major Product: CC(=O)Cc1ccc(Cl)cc1Cl
Byproduct(s): CNOC[Mg+]Br
Task: reaction
rxn_cls: Isocyanate + amine urea coupling
reactants: COC(=O)C=Cc1ccc(CN2CC(C)NC(C)C2)cc1
O=C=Nc1cccc(-n2cccc2)c1
rxn_smiles: COC(=O)C=Cc1ccc(CN2CC(C)NC(C)C2)cc1.O=C=Nc1cccc(-n2cccc2)c1>>COC(=O)C=Cc1ccc(CN2CC(C)N(C(=O)Nc3cccc(-n4cccc4)c3)C(C)C2)cc1
Answer: {"Major Product": "COC(=O)C=Cc1ccc(CN2CC(C)N(C(=O)Nc3cccc(-n4cccc4)c3)C(C)C2)cc1", "Byproduct(s)": []}
Task: reaction
rxn_cls: Sulfonamide Schotten-Baumann
reactants: CC(C)(C)OC(=O)n1c(-c2cc(S(=O)(=O)Cl)ccc2N2CCCC2)cc2ccccc21
CNCCN1CCOCC1
reagents: ClCCl
rxn_smiles: CC(C)(C)OC(=O)n1c(-c2cc(S(=O)(=O)Cl)ccc2N2CCCC2)cc2ccccc21.CNCCN1CCOCC1>ClCCl>CN(CCN1CCOCC1)S(=O)(=O)c1ccc(N2CCCC2)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)c1
Answer: Major Product: CN(CCN1CCOCC1)S(=O)(=O)c1ccc(N2CCCC2)c(-c2cc3ccccc3n2C(=O)OC(C)(C)C)c1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Mitsunobu sulfonamide reaction
reactants: CCOC(=O)CC(c1ccc(C)c(CO)c1)c1ccc2c(nnn2C)c1C
O=S1(=O)NCCOc2ccncc21
reagents: O=C(N=NC(=O)N1CCCCC1)N1CCCCC1
CCCCP(CCCC)CCCC
C1CCOC1
rxn_smiles: CCOC(=O)CC(c1ccc(C)c(CO)c1)c1ccc2c(nnn2C)c1C.O=S1(=O)NCCOc2ccncc21>O=C(N=NC(=O)N1CCCCC1)N1CCCCC1.CCCCP(CCCC)CCCC.C1CCOC1>CCOC(=O)CC(c1ccc(C)c(CN2CCOc3ccncc3S2(=O)=O)c1)c1ccc2c(nnn2C)c1C
Answer: Major Product: CCOC(=O)CC(c1ccc(C)c(CN2CCOc3ccncc3S2(=O)=O)c1)c1ccc2c(nnn2C)c1C
Byproduct(s): CCCCP(=O)(CCCC)CCCCO=C(NNC(=O)N1CCCCC1)N1CCCCC1
Task: reaction
rxn_cls: Iodo N-alkylation
reactants: CC12CCC(c3c1[nH]n(-c1ccccc1F)c3=O)C2(C)C
CCCI
rxn_smiles: CC12CCC(c3c1[nH]n(-c1ccccc1F)c3=O)C2(C)C.CCCI>>CCCn1c2c(c(=O)n1-c1ccccc1F)C1CCC2(C)C1(C)C
Answer: Major Product: CCCn1c2c(c(=O)n1-c1ccccc1F)C1CCC2(C)C1(C)C
Byproduct(s): [I-]
Task: reaction
rxn_cls: Hydroxy to chloro
reactants: Cc1ccc(C)c2c(C(C)C)cc(O)nc12
O=P(Cl)(Cl)Cl
reagents: Cc1ccccc1
rxn_smiles: Cc1ccc(C)c2c(C(C)C)cc(O)nc12.O=P(Cl)(Cl)Cl>Cc1ccccc1>Cc1ccc(C)c2c(C(C)C)cc(Cl)nc12
Answer: Major Product: Cc1ccc(C)c2c(C(C)C)cc(Cl)nc12
Byproduct(s): O=P(=O)Cl[Cl-]
Task: reaction
rxn_cls: Ketone Dess-Martin oxidation
reactants: CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21
O=C(C1CCC(O)c2nn(Cc3ccc(C(F)(F)F)nc3)c(=O)n21)N1CCC(F)C1
rxn_smiles: CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21.O=C(C1CCC(O)c2nn(Cc3ccc(C(F)(F)F)nc3)c(=O)n21)N1CCC(F)C1>>O=C1CCC(C(=O)N2CCC(F)C2)n2c1nn(Cc1ccc(C(F)(F)F)nc1)c2=O
Answer: Major Product: O=C1CCC(C(=O)N2CCC(F)C2)n2c1nn(Cc1ccc(C(F)(F)F)nc1)c2=O
Byproduct(s): CC(=O)OCC(=O)OI1OC(=O)c2ccccc-21CC(=O)[O-]
Task: reaction
rxn_cls: Iodo Miyaura boration
reactants: CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C
COc1ncnc(OC)c1I
reagents: C1=CC([Fe]C2(P(c3ccccc3)c3ccccc3)C=CC=C2)(P(c2ccccc2)c2ccccc2)C=C1
C1COCCO1
CC(=O)O[K]
Cl[Pd]Cl
rxn_smiles: CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COc1ncnc(OC)c1I>C1=CC([Fe]C2(P(c3ccccc3)c3ccccc3)C=CC=C2)(P(c2ccccc2)c2ccccc2)C=C1.C1COCCO1.CC(=O)O[K].Cl[Pd]Cl>COc1ncnc(OC)c1B1OC(C)(C)C(C)(C)O1
Answer: Major Product: COc1ncnc(OC)c1B1OC(C)(C)C(C)(C)O1
Byproduct(s): CC1(C)OB(Cl)OC1(C)CCC1(C)OB(I)OC1(C)CCl[Pd]I
Task: reaction
rxn_cls: SNAr ether synthesis
reactants: CC(C)(C)c1sc2ncnc(Cl)c2c1-c1ccc(Cl)c(Cl)c1
Oc1ccccc1OC(F)(F)F
reagents: O=S(=O)(O)O[K]
CN(C)C=O
[NaH]
rxn_smiles: CC(C)(C)c1sc2ncnc(Cl)c2c1-c1ccc(Cl)c(Cl)c1.Oc1ccccc1OC(F)(F)F>O=S(=O)(O)O[K].CN(C)C=O.[NaH]>CC(C)(C)c1sc2ncnc(Oc3ccccc3OC(F)(F)F)c2c1-c1ccc(Cl)c(Cl)c1
Answer: Major Product: CC(C)(C)c1sc2ncnc(Oc3ccccc3OC(F)(F)F)c2c1-c1ccc(Cl)c(Cl)c1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Bromination
reactants: CCc1nc2ncc(C(F)(F)F)cn2c1C(=O)c1ccc(O)c(C(F)(F)F)c1
O=C1CCC(=O)N1Br
reagents: CN(C)C=O
rxn_smiles: CCc1nc2ncc(C(F)(F)F)cn2c1C(=O)c1ccc(O)c(C(F)(F)F)c1.O=C1CCC(=O)N1Br>CN(C)C=O>CCc1nc2ncc(C(F)(F)F)cn2c1C(=O)c1cc(Br)c(O)c(C(F)(F)F)c1
Answer: Major Product: CCc1nc2ncc(C(F)(F)F)cn2c1C(=O)c1cc(Br)c(O)c(C(F)(F)F)c1
Byproduct(s): O=C1CCC(=O)N1
Task: reaction
rxn_cls: CO2H-Et deprotection
reactants: CCOC(=O)c1c(C)nc2c(OCc3c(F)ccc(OC)c3F)cc(C)cn12
reagents: O
O[Na]
C1COCCO1
rxn_smiles: CCOC(=O)c1c(C)nc2c(OCc3c(F)ccc(OC)c3F)cc(C)cn12>O.O[Na].C1COCCO1>COc1ccc(F)c(COc2cc(C)cn3c(C(=O)O)c(C)nc23)c1F
Answer: Major Product: COc1ccc(F)c(COc2cc(C)cn3c(C(=O)O)c(C)nc23)c1F
Byproduct(s): CCO[Na+]
Task: reaction
rxn_cls: N-Cbz deprotection
reactants: Br
CC(Nc1nccc(-n2cnc3ccccc32)n1)C1CN(C(=O)Nc2cccc3ccccc23)CCN1C(=O)OCc1ccccc1
rxn_smiles: Br.CC(Nc1nccc(-n2cnc3ccccc32)n1)C1CN(C(=O)Nc2cccc3ccccc23)CCN1C(=O)OCc1ccccc1>>CC(Nc1nccc(-n2cnc3ccccc32)n1)C1CN(C(=O)Nc2cccc3ccccc23)CCN1
Answer: Major Product: CC(Nc1nccc(-n2cnc3ccccc32)n1)C1CN(C(=O)Nc2cccc3ccccc23)CCN1
Byproduct(s): BrCc1ccccc1O=C=O
Task: reaction
rxn_cls: Sulfonic ester Schotten-Baumann
reactants: O=[N+]([O-])c1ccccc1S(=O)(=O)N(Cc1ccc(CO)cc1)Cc1ccccn1
CS(=O)(=O)Cl
reagents: CCN(CC)CC
O=C(O)O[Na]
ClCCl
rxn_smiles: O=[N+]([O-])c1ccccc1S(=O)(=O)N(Cc1ccc(CO)cc1)Cc1ccccn1.CS(=O)(=O)Cl>CCN(CC)CC.O=C(O)O[Na].ClCCl>CS(=O)(=O)OCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1
Answer: Major Product: CS(=O)(=O)OCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1
Byproduct(s): [Cl-]
Task: reaction
rxn_cls: Fischer-Speier esterification
reactants: CCO
Cc1ccc2c(C(=O)O)cccc2n1
reagents: O=S(=O)(O)O
ClCCl
rxn_smiles: CCO.Cc1ccc2c(C(=O)O)cccc2n1>O=S(=O)(O)O.ClCCl>CCOC(=O)c1cccc2nc(C)ccc12
Answer: Major Product: CCOC(=O)c1cccc2nc(C)ccc12
Byproduct(s): O
Task: reaction
rxn_cls: Bromo Buchwald-Hartwig amination
reactants: CC1(C)c2ccccc2-c2cc3c(cc21)[nH]c1ccc(-c2ccc4c(c2)c2cc5c(cc2n4-c2ccccc2)oc2ccccc25)cc13
Brc1ccccc1
reagents: O=C(C=Cc1ccccc1)C=Cc1ccccc1
O=C(C=Cc1ccccc1)C=Cc1ccccc1
O=C(C=Cc1ccccc1)C=Cc1ccccc1
CC(C)(C)P(C(C)(C)C)C(C)(C)C
Cc1ccccc1C
CC(C)(C)O[Na]
[Pd]
[Pd]
rxn_smiles: CC1(C)c2ccccc2-c2cc3c(cc21)[nH]c1ccc(-c2ccc4c(c2)c2cc5c(cc2n4-c2ccccc2)oc2ccccc25)cc13.Brc1ccccc1>O=C(C=Cc1ccccc1)C=Cc1ccccc1.O=C(C=Cc1ccccc1)C=Cc1ccccc1.O=C(C=Cc1ccccc1)C=Cc1ccccc1.CC(C)(C)P(C(C)(C)C)C(C)(C)C.Cc1ccccc1C.CC(C)(C)O[Na].[Pd].[Pd]>CC1(C)c2ccccc2-c2cc3c4cc(-c5ccc6c(c5)c5cc7c(cc5n6-c5ccccc5)oc5ccccc57)ccc4n(-c4ccccc4)c3cc21
Answer: Major Product: CC1(C)c2ccccc2-c2cc3c4cc(-c5ccc6c(c5)c5cc7c(cc5n6-c5ccccc5)oc5ccccc57)ccc4n(-c4ccccc4)c3cc21
Byproduct(s): CC(C)(C)O[Br-][Na+]
Task: reaction
rxn_cls: Darzens bromination
reactants: COc1c(O)ccc2c(=O)cc(-c3ccc(CCCCO)cc3)oc12
O=S(Br)Br
reagents: CN(C)C=O
ClCCl
rxn_smiles: COc1c(O)ccc2c(=O)cc(-c3ccc(CCCCO)cc3)oc12.O=S(Br)Br>CN(C)C=O.ClCCl>COc1c(O)ccc2c(=O)cc(-c3ccc(CCCCBr)cc3)oc12
Answer: Major Product: COc1c(O)ccc2c(=O)cc(-c3ccc(CCCCBr)cc3)oc12
Byproduct(s): O=S([O-])Br
Task: reaction
rxn_cls: Iodination
reactants: CN(C)CCCOc1cc(N)c(C#N)c(F)c1
O=C1CCC(=O)N1I
reagents: CC(=O)O
rxn_smiles: CN(C)CCCOc1cc(N)c(C#N)c(F)c1.O=C1CCC(=O)N1I>CC(=O)O>CN(C)CCCOc1cc(N)c(C#N)c(F)c1I
Answer: Major Product: CN(C)CCCOc1cc(N)c(C#N)c(F)c1I
Byproduct(s): O=C1CCC(=O)N1
Task: reaction
rxn_cls: Methyl esterification
reactants: CO
CC(c1cc(C(=O)O)cc2c(=O)cc(N3CCOCC3)oc12)N(C)c1cc(F)cc(F)c1
reagents: COC(=O)c1cc(C(C)Br)c2oc(N3CCOCC3)cc(=O)c2c1
CNc1cc(F)cc(F)c1
[K]I
rxn_smiles: CO.CC(c1cc(C(=O)O)cc2c(=O)cc(N3CCOCC3)oc12)N(C)c1cc(F)cc(F)c1>COC(=O)c1cc(C(C)Br)c2oc(N3CCOCC3)cc(=O)c2c1.CNc1cc(F)cc(F)c1.[K]I>COC(=O)c1cc(C(C)N(C)c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1
Answer: Major Product: COC(=O)c1cc(C(C)N(C)c2cc(F)cc(F)c2)c2oc(N3CCOCC3)cc(=O)c2c1
Byproduct(s): O
Task: reaction
rxn_cls: Iodo Sonogashira coupling
reactants: COC(=O)c1nc(I)c(NC(=O)OC(C)(C)C)s1
C#Cc1cn2ncnc2c(C)c1C
reagents: c1ccc(P(c2ccccc2)c2ccccc2)cc1
CCN(C(C)C)C(C)C
Cc1ccccc1
[Cu]I
rxn_smiles: COC(=O)c1nc(I)c(NC(=O)OC(C)(C)C)s1.C#Cc1cn2ncnc2c(C)c1C>c1ccc(P(c2ccccc2)c2ccccc2)cc1.CCN(C(C)C)C(C)C.Cc1ccccc1.[Cu]I>COC(=O)c1nc(C#Cc2cn3ncnc3c(C)c2C)c(NC(=O)OC(C)(C)C)s1
Answer: Major Product: COC(=O)c1nc(C#Cc2cn3ncnc3c(C)c2C)c(NC(=O)OC(C)(C)C)s1
Byproduct(s): Cl[Cu]Cl[Pd]II[Cu]I
Task: reaction
rxn_cls: Ketone to alcohol reduction
reactants: CC(C)(Cc1ccccc1)C(=O)C=CI
[BH4-]
rxn_smiles: CC(C)(Cc1ccccc1)C(=O)C=CI.[BH4-]>>CC(C)(Cc1ccccc1)C(O)C=CI
Answer: Major Product: CC(C)(Cc1ccccc1)C(O)C=CI
Byproduct(s): B
Task: reaction
rxn_cls: Iodo N-methylation
reactants: CI
COC(=O)CC1NC(=O)c2cc(OCc3cccc(-c4ccc(Cl)cc4C)c3)ccc21
rxn_smiles: CI.COC(=O)CC1NC(=O)c2cc(OCc3cccc(-c4ccc(Cl)cc4C)c3)ccc21>>COC(=O)CC1c2ccc(OCc3cccc(-c4ccc(Cl)cc4C)c3)cc2C(=O)N1C
Answer: Major Product: COC(=O)CC1c2ccc(OCc3cccc(-c4ccc(Cl)cc4C)c3)cc2C(=O)N1C
Byproduct(s): [I-]
Task: reaction
rxn_cls: Aldehyde Dess-Martin oxidation
reactants: COc1ccc2c(Nc3c(Cl)cncc3Cl)cc(=O)n(CCO)c2c1OC1CCCC1
reagents: CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21
rxn_smiles: COc1ccc2c(Nc3c(Cl)cncc3Cl)cc(=O)n(CCO)c2c1OC1CCCC1>CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21>COc1ccc2c(Nc3c(Cl)cncc3Cl)cc(=O)n(CC=O)c2c1OC1CCCC1
Answer: Major Product: COc1ccc2c(Nc3c(Cl)cncc3Cl)cc(=O)n(CC=O)c2c1OC1CCCC1
Byproduct(s): CC(=O)OCC(=O)OI1OC(=O)c2ccccc-21CC(=O)[O-]
Task: reaction
rxn_cls: Ketone reductive amination
reactants: COC(=O)C1CN(C(=O)OC(C)(C)C)CCC1=O
C1CNC1
reagents: CC(=O)O[BH-](OC(C)=O)OC(C)=O
ClCCCl
O
[Na+]
rxn_smiles: COC(=O)C1CN(C(=O)OC(C)(C)C)CCC1=O.C1CNC1>CC(=O)O[BH-](OC(C)=O)OC(C)=O.ClCCCl.O.[Na+]>COC(=O)C1CN(C(=O)OC(C)(C)C)CCC1N1CCC1
Answer: Major Product: COC(=O)C1CN(C(=O)OC(C)(C)C)CCC1N1CCC1
Byproduct(s): CC(=O)OB(OC(C)=O)OC(C)=OO
Task: reaction
rxn_cls: Keto alpha-alkylation
reactants: CN1CC(=O)N(C)C(C)(Cc2ccccc2)C1=O
Clc1cccc(CBr)c1Cl
reagents: O
CN(C)C=O
[NaH]
rxn_smiles: CN1CC(=O)N(C)C(C)(Cc2ccccc2)C1=O.Clc1cccc(CBr)c1Cl>O.CN(C)C=O.[NaH]>CN1C(=O)C(C)(Cc2ccccc2)N(C)C(=O)C1Cc1cccc(Cl)c1Cl
Answer: Major Product: CN1C(=O)C(C)(Cc2ccccc2)N(C)C(=O)C1Cc1cccc(Cl)c1Cl
Byproduct(s): [Br-]
Task: reaction
rxn_cls: Triflyloxy Miyaura boration
reactants: CCS(=O)(=O)c1ccc(-c2cc(OS(=O)(=O)C(F)(F)F)ccc2F)c(C#N)c1
CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C
reagents: C1COCCO1
CC(=O)O[K]
N#N
rxn_smiles: CCS(=O)(=O)c1ccc(-c2cc(OS(=O)(=O)C(F)(F)F)ccc2F)c(C#N)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C>C1COCCO1.CC(=O)O[K].N#N>CCS(=O)(=O)c1ccc(-c2cc(B3OC(C)(C)C(C)(C)O3)ccc2F)c(C#N)c1
Answer: Major Product: CCS(=O)(=O)c1ccc(-c2cc(B3OC(C)(C)C(C)(C)O3)ccc2F)c(C#N)c1
Byproduct(s): CC1(C)OB(Cl)OC1(C)CCC1(C)OB(OS(=O)(=O)C(F)(F)F)OC1(C)CO=S(=O)(O[Pd]Cl)C(F)(F)F
Task: reaction
rxn_cls: Chlorination
reactants: Nc1c(C(=O)O)ccc(Br)c1F
O=C1CCC(=O)N1Cl
reagents: CN(C)C=O
rxn_smiles: Nc1c(C(=O)O)ccc(Br)c1F.O=C1CCC(=O)N1Cl>CN(C)C=O>Nc1c(C(=O)O)cc(Cl)c(Br)c1F
Answer: Major Product: Nc1c(C(=O)O)cc(Cl)c(Br)c1F
Byproduct(s): O=C1CCC(=O)N1
Task: reaction
rxn_cls: Chloro Miyaura boration
reactants: CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C
Cc1cc(-c2ccccc2)nc2cc(Cl)ccc12
reagents: CCCc1cccc(CCC)c1-n1cc[n+](-c2c(CCC)cccc2CCC)c1
CC(=O)O[Pd]OC(C)=O
CC(=O)O[K]
C1CCOC1
[Cl-]
rxn_smiles: CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.Cc1cc(-c2ccccc2)nc2cc(Cl)ccc12>CCCc1cccc(CCC)c1-n1cc[n+](-c2c(CCC)cccc2CCC)c1.CC(=O)O[Pd]OC(C)=O.CC(=O)O[K].C1CCOC1.[Cl-]>Cc1cc(-c2ccccc2)nc2cc(B3OC(C)(C)C(C)(C)O3)ccc12
Answer: Major Product: Cc1cc(-c2ccccc2)nc2cc(B3OC(C)(C)C(C)(C)O3)ccc12
Byproduct(s): CC1(C)OB(Cl)OC1(C)C
Task: reaction
rxn_cls: Ester hydrolysis
reactants: CCCCCCCCCCOC(C)c1ccc(C(=O)OCCCC)cc1
reagents: O[Na]
C1CCOC1
rxn_smiles: CCCCCCCCCCOC(C)c1ccc(C(=O)OCCCC)cc1>O[Na].C1CCOC1>CCCCCCCCCCOC(C)c1ccc(C(=O)O)cc1
Answer: Major Product: CCCCCCCCCCOC(C)c1ccc(C(=O)O)cc1
Byproduct(s): CCCCO[Na+]
Task: reaction
rxn_cls: O-TBDPS deprotection
reactants: CC(C)(C)S(=O)N1Cc2cc(C(N)=O)nc(-c3cccc(-c4cccnc4)c3)c2C1CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
[F-]
rxn_smiles: CC(C)(C)S(=O)N1Cc2cc(C(N)=O)nc(-c3cccc(-c4cccnc4)c3)c2C1CCO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C.[F-]>>CC(C)(C)S(=O)N1Cc2cc(C(N)=O)nc(-c3cccc(-c4cccnc4)c3)c2C1CCO
Answer: Major Product: CC(C)(C)S(=O)N1Cc2cc(C(N)=O)nc(-c3cccc(-c4cccnc4)c3)c2C1CCO
Byproduct(s): CC(C)(C)[Si](F)(c1ccccc1)c1ccccc1
Task: reaction
rxn_cls: Grignard ester substitution
reactants: COC(=O)C(=O)OC
CCCCCC[Mg]Br
reagents: C1CCOC1
rxn_smiles: COC(=O)C(=O)OC.CCCCCC[Mg]Br>C1CCOC1>CCCCCCC(=O)C(=O)OC
Answer: Major Product: CCCCCCC(=O)C(=O)OC
Byproduct(s): C[O-][Mg+]Br
Task: reaction
rxn_cls: Bromo Suzuki coupling
reactants: CC(C)C(O)(c1cccc(Br)c1)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1
OB(O)c1ccsc1
reagents: c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Cc1ccccc1
O=C(O[Na])O[Na]
CCO
O
rxn_smiles: CC(C)C(O)(c1cccc(Br)c1)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1.OB(O)c1ccsc1>c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.Cc1ccccc1.O=C(O[Na])O[Na].CCO.O>CC(C)C(O)(c1cccc(-c2ccsc2)c1)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1
Answer: Major Product: CC(C)C(O)(c1cccc(-c2ccsc2)c1)c1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1
Byproduct(s): CCOB(O)OO=C(O[Na])OB(O)OOB(O)O[Br-][Na+]c1ccc(P(c2ccccc2)c2ccccc2)cc1c1ccc(P(c2ccccc2)c2ccccc2)cc1
Task: reaction
rxn_cls: Iodo Stille reaction
reactants: O=c1c(I)c(OCc2ccc(F)cc2)ccn1Cc1cccc(F)c1
C[Sn](C)(C)C
reagents: c1ccc(P(c2ccccc2)c2ccccc2)cc1
c1ccc(P(c2ccccc2)c2ccccc2)cc1
CN(C)C=O
Cl[Pd]Cl
N#N
[Li]Cl
rxn_smiles: O=c1c(I)c(OCc2ccc(F)cc2)ccn1Cc1cccc(F)c1.C[Sn](C)(C)C>c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.CN(C)C=O.Cl[Pd]Cl.N#N.[Li]Cl>Cc1c(OCc2ccc(F)cc2)ccn(Cc2cccc(F)c2)c1=O
Answer: Major Product: Cc1c(OCc2ccc(F)cc2)ccn(Cc2cccc(F)c2)c1=O
Byproduct(s): C[Pd]ClC[Sn](C)(C)ClC[Sn](C)(C)ICl[Pd]I
Task: reaction
rxn_cls: Bromo Sonogashira coupling
reactants: CCCCCc1ccc(Br)cc1
C#CC(C)(C)O
reagents: Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
c1ccc(P(c2ccccc2)c2ccccc2)cc1
CCN(CC)CC
[C-]#[O+]
[Cu]I
rxn_smiles: CCCCCc1ccc(Br)cc1.C#CC(C)(C)O>Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.CCN(CC)CC.[C-]#[O+].[Cu]I>CCCCCc1ccc(C#CC(C)(C)O)cc1
Answer: Major Product: CCCCCc1ccc(C#CC(C)(C)O)cc1
Byproduct(s): Cl[Cu]Cl[Pd](Br)P(c1ccccc1)(c1ccccc1)c1ccccc1I[Cu]Brc1ccc(P(c2ccccc2)c2ccccc2)cc1
Task: reaction
rxn_cls: O-Bn deprotection
reactants: O=c1c(OCc2ccccc2)cn(-c2ccc(N3CC(F)(F)C3)cc2F)nc1-c1ccnn1-c1ccccc1
reagents: CO
CCOC(C)=O
[Pd]
[H][H]
rxn_smiles: O=c1c(OCc2ccccc2)cn(-c2ccc(N3CC(F)(F)C3)cc2F)nc1-c1ccnn1-c1ccccc1>CO.CCOC(C)=O.[Pd].[H][H]>O=c1c(O)cn(-c2ccc(N3CC(F)(F)C3)cc2F)nc1-c1ccnn1-c1ccccc1
Answer: Major Product: O=c1c(O)cn(-c2ccc(N3CC(F)(F)C3)cc2F)nc1-c1ccnn1-c1ccccc1
Byproduct(s): CCCC(=O)OCC=OCCOCc1ccccc1O=c1ccn(-c2ccc(N3CC(F)(F)C3)cc2F)nc1-c1ccnn1-c1ccccc1OCc1ccccc1
Task: reaction
rxn_cls: Chloro Sonogashira coupling
reactants: CCOC(=O)Cc1cncnc1Cl
C#C[Si](CC)(CC)CC
reagents: c1ccc(P(c2ccccc2)c2ccccc2)cc1
CCN(CC)CC
CN(C)C=O
N#N
rxn_smiles: CCOC(=O)Cc1cncnc1Cl.C#C[Si](CC)(CC)CC>c1ccc(P(c2ccccc2)c2ccccc2)cc1.CCN(CC)CC.CN(C)C=O.N#N>CCOC(=O)Cc1cncnc1C#C[Si](CC)(CC)CC
Answer: Major Product: CCOC(=O)Cc1cncnc1C#C[Si](CC)(CC)CC
Byproduct(s): Cl[Cu]IIc1ccc(P(c2ccccc2)c2ccccc2)cc1
Task: reaction
rxn_cls: Alcohol + amine condensation
reactants: CC(C)(O)C1CCNC1
CC(C)NC(=O)C1CCC(n2c(=NC(=O)c3ccc(F)cc3)[nH]c3ccc(CO)cc32)CC1
O=S(Cl)Cl
rxn_smiles: CC(C)(O)C1CCNC1.CC(C)NC(=O)C1CCC(n2c(=NC(=O)c3ccc(F)cc3)[nH]c3ccc(CO)cc32)CC1.O=S(Cl)Cl>>CC(C)NC(=O)C1CCC(n2c(=NC(=O)c3ccc(F)cc3)[nH]c3ccc(CN4CCC(C(C)(C)O)C4)cc32)CC1
Answer: Major Product: CC(C)NC(=O)C1CCC(n2c(=NC(=O)c3ccc(F)cc3)[nH]c3ccc(CN4CCC(C(C)(C)O)C4)cc32)CC1
Byproduct(s): O=S=O[Cl-][Cl-]
Task: reaction
rxn_cls: O-TBS deprotection
reactants: C=CCOC(=O)NC(C(=O)NC(C)C(=O)Nc1ccc(COC(=O)N2c3cc(OCCCCCOc4cc5c(cc4OC)C(=O)N4C=C(c6ccc(OC)cc6)CC4CN5C(=O)OCC=C)c(OC)cc3C(=O)N3CC4(CC4)CC3C2O[Si](C)(C)C(C)(C)C)cc1)C(C)C
[F-]
rxn_smiles: C=CCOC(=O)NC(C(=O)NC(C)C(=O)Nc1ccc(COC(=O)N2c3cc(OCCCCCOc4cc5c(cc4OC)C(=O)N4C=C(c6ccc(OC)cc6)CC4CN5C(=O)OCC=C)c(OC)cc3C(=O)N3CC4(CC4)CC3C2O[Si](C)(C)C(C)(C)C)cc1)C(C)C.[F-]>>C=CCOC(=O)NC(C(=O)NC(C)C(=O)Nc1ccc(COC(=O)N2c3cc(OCCCCCOc4cc5c(cc4OC)C(=O)N4C=C(c6ccc(OC)cc6)CC4CN5C(=O)OCC=C)c(OC)cc3C(=O)N3CC4(CC4)CC3C2O)cc1)C(C)C
Answer: Major Product: C=CCOC(=O)NC(C(=O)NC(C)C(=O)Nc1ccc(COC(=O)N2c3cc(OCCCCCOc4cc5c(cc4OC)C(=O)N4C=C(c6ccc(OC)cc6)CC4CN5C(=O)OCC=C)c(OC)cc3C(=O)N3CC4(CC4)CC3C2O)cc1)C(C)C
Byproduct(s): CC(C)(C)[Si](C)(C)F
Task: reaction
rxn_cls: Mitsunobu aryl ether synthesis
reactants: Cc1onc(-c2ccccc2)c1-c1nnc2n1Cc1ccc(O)cc1-2
CC(C)(C)OC(=O)N1CCC(O)CC1
reagents: c1ccc(P(c2ccccc2)c2ccccc2)cc1
CCOC(=O)N=NC(=O)OCC
O=C(O)C(F)(F)F
ClCCl
[C-]#[O+]
rxn_smiles: Cc1onc(-c2ccccc2)c1-c1nnc2n1Cc1ccc(O)cc1-2.CC(C)(C)OC(=O)N1CCC(O)CC1>c1ccc(P(c2ccccc2)c2ccccc2)cc1.CCOC(=O)N=NC(=O)OCC.O=C(O)C(F)(F)F.ClCCl.[C-]#[O+]>Cc1onc(-c2ccccc2)c1-c1nnc2n1Cc1ccc(OC3CCN(C(=O)OC(C)(C)C)CC3)cc1-2
Answer: Major Product: Cc1onc(-c2ccccc2)c1-c1nnc2n1Cc1ccc(OC3CCN(C(=O)OC(C)(C)C)CC3)cc1-2
Byproduct(s): CCOC(=O)NNC(=O)OCCO=P(c1ccccc1)(c1ccccc1)c1ccccc1
Task: reaction
rxn_cls: Chloro Buchwald-Hartwig amination
reactants: COc1ccc(-c2noc(C3CCN(C(=O)CN)CC3)n2)cc1OC
Clc1nccc2ccccc12
reagents: c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1
CC(=O)O[Pd]OC(C)=O
Cc1ccccc1
O=C(O[Cs])O[Cs]
N#N
rxn_smiles: COc1ccc(-c2noc(C3CCN(C(=O)CN)CC3)n2)cc1OC.Clc1nccc2ccccc12>c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1.CC(=O)O[Pd]OC(C)=O.Cc1ccccc1.O=C(O[Cs])O[Cs].N#N>COc1ccc(-c2noc(C3CCN(C(=O)CNc4nccc5ccccc45)CC3)n2)cc1OC
Answer: Major Product: COc1ccc(-c2noc(C3CCN(C(=O)CNc4nccc5ccccc45)CC3)n2)cc1OC
Byproduct(s): CC(=O)OCC(=O)O[Pd]ClCC(=O)O[Pd]OC(=O)O[Cs]O=C(O)O[Cs][Cl-][Cs+]
Task: reaction
rxn_cls: Weinreb amide synthesis
reactants: CCCC(C)(C)C(=O)O
CNOC
reagents: Cl
CCN=C=NCCCN(C)C
CN1CCOCC1
On1nnc2ccccc21
ClCCl
rxn_smiles: CCCC(C)(C)C(=O)O.CNOC>Cl.CCN=C=NCCCN(C)C.CN1CCOCC1.On1nnc2ccccc21.ClCCl>CCCC(C)(C)C(=O)N(C)OC
Answer: Major Product: CCCC(C)(C)C(=O)N(C)OC
Byproduct(s): [OH-]
Task: reaction
rxn_cls: Iodo Grignard reaction
reactants: CC(C)(C)OC(=O)N1CCC(C=O)C1
C[Mg]I
reagents: C1CCOC1
[C-]#[O+]
rxn_smiles: CC(C)(C)OC(=O)N1CCC(C=O)C1.C[Mg]I>C1CCOC1.[C-]#[O+]>CC(O)C1CCN(C(=O)OC(C)(C)C)C1
Answer: Major Product: CC(O)C1CCN(C(=O)OC(C)(C)C)C1
Byproduct(s): [CH3-][Mg+]I
Task: reaction
rxn_cls: Bromo Miyaura boration
reactants: CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C
CSc1ccc(Br)cn1
reagents: CC(=O)O[K]
CS(C)=O
[Pd]
rxn_smiles: CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CSc1ccc(Br)cn1>CC(=O)O[K].CS(C)=O.[Pd]>CSc1ccc(B2OC(C)(C)C(C)(C)O2)cn1
Answer: Major Product: CSc1ccc(B2OC(C)(C)C(C)(C)O2)cn1
Byproduct(s): CC1(C)OB(Br)OC1(C)C
Task: reaction
rxn_cls: Bromo Stille reaction
reactants: C=C[Sn](CCCC)(CCCC)CCCC
CC(=O)CCC(=O)c1ccc(Br)cc1
reagents: c1ccc(P(c2ccccc2)c2ccccc2)cc1
c1ccc(P(c2ccccc2)c2ccccc2)cc1
c1ccc(P(c2ccccc2)c2ccccc2)cc1
c1ccc(P(c2ccccc2)c2ccccc2)cc1
Cc1ccccc1
F[Na]
[Pd]
rxn_smiles: C=C[Sn](CCCC)(CCCC)CCCC.CC(=O)CCC(=O)c1ccc(Br)cc1>c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.Cc1ccccc1.F[Na].[Pd]>C=Cc1ccc(C(=O)CCC(C)=O)cc1
Answer: Major Product: C=Cc1ccc(C(=O)CCC(C)=O)cc1
Byproduct(s): C=C[Sn](Br)(CCCC)CCCCCCCC[Sn](Br)(CCCC)CCCCCCCCc1ccc(C(=O)CCC(C)=O)cc1
Task: reaction
rxn_cls: Chloro Suzuki coupling
reactants: CC(C)(C)P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C
Clc1ccc2c(c1)C1(c3ccccc3O2)C2CC3CC(C2)CC1C3
O=C(O[K])O[K]
OB(O)c1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc3ccccc3c2)cc1
rxn_smiles: CC(C)(C)P([Pd]P(C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C.Clc1ccc2c(c1)C1(c3ccccc3O2)C2CC3CC(C2)CC1C3.O=C(O[K])O[K].OB(O)c1ccc(N(c2ccc(-c3ccccc3)cc2)c2ccc3ccccc3c2)cc1>>c1ccc(-c2ccc(N(c3ccc(-c4ccc5c(c4)C4(c6ccccc6O5)C5CC6CC(C5)CC4C6)cc3)c3ccc4ccccc4c3)cc2)cc1
Answer: Major Product: c1ccc(-c2ccc(N(c3ccc(-c4ccc5c(c4)C4(c6ccccc6O5)C5CC6CC(C5)CC4C6)cc3)c3ccc4ccccc4c3)cc2)cc1
Byproduct(s): O=C(O[K])OB(O)O[Cl-][K+]
Task: reaction
rxn_cls: Carboxylic acid + amine condensation
reactants: CN1C(=O)C(N)N=C(c2ccccc2)c2ccccc21
O=C(O)C(Cc1ccc(Cl)c(Cl)c1)c1ccccc1
rxn_smiles: CN1C(=O)C(N)N=C(c2ccccc2)c2ccccc21.O=C(O)C(Cc1ccc(Cl)c(Cl)c1)c1ccccc1>>CN1C(=O)C(NC(=O)C(Cc2ccc(Cl)c(Cl)c2)c2ccccc2)N=C(c2ccccc2)c2ccccc21
Answer: Major Product: CN1C(=O)C(NC(=O)C(Cc2ccc(Cl)c(Cl)c2)c2ccccc2)N=C(c2ccccc2)c2ccccc21
Byproduct(s): [OH-]
Task: reaction
rxn_cls: Darzens chlorination
reactants: COC(=O)CC(O)(CCCC(C)(C)O)C(=O)OC1C(OC)=CC23CCCN2CCc2cc4c(cc2C13)OCO4
O=S(Cl)Cl
rxn_smiles: COC(=O)CC(O)(CCCC(C)(C)O)C(=O)OC1C(OC)=CC23CCCN2CCc2cc4c(cc2C13)OCO4.O=S(Cl)Cl>>COC(=O)CC(O)(CCCC(C)(C)Cl)C(=O)OC1C(OC)=CC23CCCN2CCc2cc4c(cc2C13)OCO4
Answer: Major Product: COC(=O)CC(O)(CCCC(C)(C)Cl)C(=O)OC1C(OC)=CC23CCCN2CCc2cc4c(cc2C13)OCO4
Byproduct(s): O=S([O-])Cl
Task: reaction
rxn_cls: Wohl-Ziegler bromination
reactants: COc1cccc([N+](=O)[O-])c1C
O=C1CCC(=O)N1Br
reagents: CC(C)(C)OO
rxn_smiles: COc1cccc([N+](=O)[O-])c1C.O=C1CCC(=O)N1Br>CC(C)(C)OO>COc1cccc([N+](=O)[O-])c1CBr
Answer: Major Product: COc1cccc([N+](=O)[O-])c1CBr
Byproduct(s): BrO=C1CCC(=O)[NH]1[BrH]