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

Participants

Reaction Steps

4-bromo-2-fluorobenzoic acid (30 g, 0.14 mol) was dissolved in methanol with a few drops of sulfuric acid. The reaction medium was refluxed for 20 hours. The cooled reaction mixture was evaporated and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic layer was separated and washed with brine, dried over sodium sulfate, filtered and evaporated to give methyl 4-bromo-2-fluorobenzoate (20.7 g, yield 64%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm); 3.85 (s, 3H), 7.55-7.58 (m, 1H), 7.70-7.73 (m, 1H), 7.79-7.83 (m, 1H); LC-MS (ESI) m/z: 233 (M+1)+, 235 (M+3)+

Provenance & Evidence