Methanol → 4-Bromo-2-fluoro-benzoic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 4-bromo-2-fluorobenzoic acid (15.0 g, 68.49 mmol, 1 eq) in MeOH (150 mL), SOCl2 (23.09 mL, 136.9 mmol, 2 eq) was added at 0° C. for 15 min and the mixture was stirred at RT for 12 h. The MeOH was evaporated and the residue was diluted with ethyl acetate (250 mL), washed with a saturated aqueous solution of NaHCO3, brine (150 mL) and water (150 mL). The ethyl acetate layer was dried over Na2SO4, evaporated under vacuum to get methyl 4-bromo-2-fluorobenzoate (15 g, 93%) as an off white solid (LC-MS purity, 99%; TLC system: EtOAc/PE (3:7), Rf: 0.8).

Provenance & Evidence