Methanol → 5-Chloro-2-(trifluoromethyl)benzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve 5-chloro-2-(trifluoromethyl)benzoic acid (10 g, 0.044 mol) in MeOH (150 mL). Add thionyl chloride (50 g, 0.421 mol) slowly. Heat the resulting mixture to 70° C., and stir for 12 hours. Concentrate the mixture under reduced pressure. Pour the residue into water (100 mL), and extract the aqueous with EtOAc (2×200 mL). Dry the combined organics over sodium sulfate, and concentrate under reduced pressure to give the title compound (11.5 g, 96.5%) as an oil. 1H NMR (300 MHz, CDCl3,) δ 7.78 (d, J=2.1 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.57 (dd, J=2.1, 8.7 Hz, 1H), 3.95 (s, 3H).

Provenance & Evidence