Methanol → Methyl 4-bromo-3-(trifluoromethyl)benzoate

Participants

Reaction Steps

Thionyl chloride (16.2 mL, 223 mmol) was added dropwise over 15 min into a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (Acceledev 000625, 15.0 g, 55.8 mmol) in MeOH (300 mL). The resulting mixture was stirred at RT for 12 hours. The reaction mixture was concentrated under reduced pressure. The residue was taken up with EtOAc (500 mL) and washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure affording the title compound as an orange solid (14.8 g, 94%). HPLC (Method A), Rt 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).

Provenance & Evidence