Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:10]([CH3:14])([CH3:13])[CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=1[OH:15].Cl[C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=1[N+:28]([O-:30])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:28]([C:19]1[CH:20]=[C:21]([C:24]([F:25])([F:26])[F:27])[CH:22]=[CH:23][C:18]=1[O:15][C:5]1[CH:6]=[CH:7][C:8]([C:10]([CH3:13])([CH3:14])[CH2:11][CH3:12])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:16])([O-:30])=[O:29]
Reactant: O=[N+]([O-])c1cc(C(F)(F)F)ccc1Cl
Reactant: CCC(C)(C)c1ccc(O)c(C(=O)OC)c1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: CN(C)C=O
Product: CCC(C)(C)c1ccc(Oc2ccc(C(F)(F)F)cc2[N+](=O)[O-])c(C(=O)OC)c1

Procedure:
Methyl-2-hydroxy-5-(1,1-dimethylpropyl)benzoate (3.0 g, 0.0135 mol), 4-chloro-3-nitrobenzotrifluoride (1.94 ml, 0.013 mol) and potassium carbonate (1.1 g, 0.008 mol) were mixed in dimethylformamide (50 mL) for 3 h. The solvents were evaporated and the residue was flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CDCl3) δ8.24 (d, 1H); 7.99 (d, 1H), 7.54-7.68 (m, 2H), 7.15 (d, 1H), 6.82 (d, 1H), 3.70 (s, 3H), 1.61-1.76 (m, 2H), 1.32 (s, 6H), 0.65-0.76 (t, 3H).