Methanol → Methyl 4-amino-2-(trifluoromethyl)benzoate

Reaction equation

O=S(Cl)Cl.[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:7]=1.[CH3:19]O>>[NH2:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:19])=[O:11])=[C:8]([C:15]([F:16])([F:17])[F:18])[CH:7]=1

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 38363254-amino-2-(trifluoromethyl)benzoic Acid

Product 1

HCID 46311081Methyl 4-amino-2-(trifluoromethyl)benzoateYield 64%

Procedure

SOCl2 (1.1 mL, 14.62 mmol, 1 equiv.) was added to a solution of 4-amino-2-trifluoromethylbenzoic acid (3 g, 14.62 mmol, 1 equiv.) in 40 mL of MeOH and the reaction mixture was refluxed overnight. Solvent was removed in vacuo and the residue was taken into EtOAc and washed with sat. NaHCO3 (×2), brine and dried over MgSO4, and concentrated to give 2.06 g (Yield=64%) of product as a clear oil.