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

Participants

Reaction Steps

Combine 4-bromo-2-fluorobenzoic acid (10 g, 45.7 mmol), methanol (100 mL), and concentrated sulfuric acid (5.0 mL). Heat to reflux. After 16 h, cool to room temperature and evaporate in vacuo to afford a white solid. Dissolve the solid in ethyl acetate (about 40 mL), extract with 2×80 mL saturated aqueous sodium bicarbonate and 1×80 mL brine, dry over MgSO4, filter, and evaporate in vacuo to yield 9.32 g (88%) of methyl 4-bromo-2-fluorobenzoate as a white solid. 1H NMR (d6-DMSO, 300 MHz) 8.80 (t, J=8.4 Hz, 1H), 7.72 (dd, J=10.8 Hz, 1.8 Hz, 1H), 7.54 (ddd, J=8.4 Hz, 1.8 Hz, 0.6 Hz, 1H), 3.83 (s, 3H); IR (cm−1, KBr): 3010, 2995, 1723, 1603, 1484, 1438, 1406, 1294, 1277, 1095, 885; Anal calc'd for C8H6BrFO2: C, 41.23; H, 2.60; Found: C, 40.97; H, 2.61.

Provenance & Evidence