Reaction SMILES: [Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7](=[O:27])[CH:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.CCS.[Al](Br)(Br)Br>C(Br)Br>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7](=[O:27])[CH:8]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH3:26])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1
Reactant: COc1ccc(C2=NC(Cc3ccccc3C)C(=O)Nc3ccc(Cl)cc32)cc1
Agent: Br[Al](Br)Br
Solvent: BrCBr
Solvent: CCS
Product: Cc1ccccc1CC1N=C(c2ccc(O)cc2)c2cc(Cl)ccc2NC1=O
Temperature: 0 °C
Reaction time: 8 h
Yield: 80 %

Procedure:
To a solution of (Z)-7-chloro-5-(4-methoxyphenyl)-3-(2-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one precursor (0.6 g, 1.4 mmol) in CH2Br2 (20 mL) was added EtSH (7 mL) and then AlBr3 (1.7 g, 6.3 mmol, 4.5 eq). The resulting mixture was stirred overnight and then treated with ice (20 g) and after one hour filtered. The resulting solid was triturated with 50% DCM/heptane and then vacuum dried to give 445 mg (yield of 80%) of (Z)-7-chloro-5-(4-hydroxyphenyl)-3-(2-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one as a light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 2.31 (s, 3H), 3.25-3.45 (m, 2H), 3.73 (dd, 1H), 6.80 (d, 2H), 7.02-7.18 (m, 3H), 7.2-7.3 (m, 5H), 7.64 (dd, 1H), 10.0 (br s, 1H), 10.7 (br s, 1H). MS, m/z 391.7 [M+1] The following compounds were prepared based on the above procedure: (Z)-7-Chloro-5-(4-hydroxyphenyl)-3-(2-methylbenzyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 2.32 (s, 3H), 3.3-3.5 (m, 5H; contains singlet for NMe at 3.36), 3.90 (t, 1H), 6.87 (d, 2H), 7.05-7.15 (m, 3H), 7.20 (m, 1H), 7.29 (fine d, 1H), 7.35 (d, 2H), 7.65 (d, 1H), 7.78 (dd, 1H), 9-11 (br s, 1H). MS, m/z 405.3 [M+1]. (Z)-7-Chloro-5-(4-hydroxyphenyl)-3-(3-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 2.28 (s, 3H), 3.2-3.4 (m, 2H; contains water signal), 3.63 (t, 1H), 6.79 (d, 2H), 7.00 (d, 1H), 7.05-7.15 (m, 3H), 7.20 (m, 1H), 7.29 (fine d, 1H), 7.31 (d, 2H), 7.62 (dd, 1H), 9.95 (s, 1H), 10.61 (s, 1H). MS, m/z 391.7 [M+1]. (Z)-7-Chloro-5-(4-hydroxyphenyl)-3-(3-methylbenzyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 2.25 (s, 3H), 3.25-3.45 (m, 5H; contains singlet for NMe at 3.35), 3.83 (t, 1H), 6.87 (d, 2H), 6.99 (d, 1H), 7.05-7.2 (m, 3H), 7.28 (fine d, 1H), 7.38 (d, 2H), 7.63 (d, 1H), 7.77 (dd, 1H), 10.2 (br s, 1H). MS, m/z 405.3 [M+1]. (Z)-7-Chloro-5-(4-hydroxyphenyl)-3-(4-methylbenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 2.23 (s, 3H), 3.2-3.4 (m, 3H), 3.80 (m, 1H), 6.86 (d, 2H), 7.09 (d, 2H), 7.23 (d, 2H), 7.25-7.35 (m, 4H), 7.71 (dd, 1H), 10.3 (br s, 1H), 10.9 (br s, 1H). MS, m/z 391.8 [M+1]. (Z)-7-Chloro-5-(4-hydroxyphenyl)-3-(4-methylbenzyl)-1-methyl-1H-benzo[e][1,4]diazepin-2(3H)-one. 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 3H), 3.25-3.4 (m, 5H; contains singlet for NMe at 3.34), 3.82 (t, 1H), 6.87 (d, 2H), 7.07 (d, 2H), 7.19 (d, 2H), 7.28 (fine d, 1H), 7.37 (d, 2H), 7.63 (d, 1H), 7.76 (dd, 1H), 9.5-11 (br s, 1H). MS, m/z 405.3 [M+1]. (Z)-7-Chloro-3-(2-ethylbenzyl)-5-(4-hydroxyphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one.