Dimethylformamide → Methyl 5-bromo-2-methoxy-3-methylbenzoate

Participants

Reaction Steps

5-Bromo-2-hydroxy-3-methylbenzoic acid (2.8 g, 12.1 mmol), iodomethane (1.97 mL, 31.6 mmol) and potassium carbonate (16.9 g, 123 mmol) were combined in dimethylformamide (30 mL). After stirring at room temperature for 16 h, the solvent was removed in vacuo and the crude product dissolved in ethyl acetate, which was washed with water (2×), then brine (2×), dried over sodium sulfate, and concentrated. Flash chromatography on silica gel (10% ethyl acetate/hexanes) gave 2.26 g (72%). 1H-NMR (CDCl3, 500 MHz) δ 7.74-7.75 (m, 1H), 7.45-7.46 (m, 1H), 3.90 (s, 3H), 3.80 (s, 3H), 2.28 (s, 3H). Mass spec.: 261.08 (MH)+.

Provenance & Evidence