Methanol → Methyl 4-fluoro-3-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluoro-3-methyl-benzoic acid (27.4 g, 178.0 mmol) in methanol (200 mL) was slowly added thionyl chloride (17.8 mL, 243.3 mmol). The solution was stirred at 35° C. for 7 hours. The solution was allowed to cool to room temperature and concentrated in vacuo to an oil. This oil was dissolved in EtOAc (75 mL) and washed sequentially with saturated aqueous sodium bicarbonate solution (2×75 mL) and brine solution (1×75 mL). The organic layer was separated and dried over sodium sulfate, filtered and concentrated in vacuo to provide methyl 4-fluoro-3-methyl-benzoate (25.4 g, 85%) as a red oil. ESI-MS m/z calc. 168.0. found 169.2 (M+1)+; Retention time: 1.48 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 7.92-7.88 (m, 1H), 7.88-7.83 (m, 1H), 7.04 (t, J=8.9 Hz, 1H), 3.90 (s, 3H), 2.31 (d, J=2.0 Hz, 3H).

Provenance & Evidence