Methyl 4-Bromo-3-(Trifluoromethyl)benzoate

67-56-1

1141473-97-3

107317-58-8

Thionyl chloride (16.2 mL, 223 mmol) was slowly added dropwise to a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (15.0 g, 55.8 mmol) in methanol (300 mL) over 15 minutes. The reaction mixture was stirred at room temperature for 12 hours. Subsequently, the reaction mixture was concentrated by distillation under reduced pressure. The concentrated residue was dissolved in ethyl acetate (500 mL) and washed sequentially with saturated aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to give methyl 3-trifluoromethyl-4-bromobenzoate as an orange solid (14.8 g, 94% yield). High performance liquid chromatography (Method A) showed a retention time of 4.7 min (purity: 99.0%).1H NMR (DMSO-d6, 300 MHz) δ 8.26 (m, 1H), 8.14 (m, 2H), 3.93 (s, 3H).