Methanol → Methyl 3-bromo-5-methoxybenzoate

Participants

Reaction Steps

To a stirred mixture of crude 3-bromo-5-methoxybenzoic acid (40% purity, 0.8 g, 1.4 mmol) in CH2Cl2 (50 mL) at 0° C. were added DMF (0.1 mL) and acetyl chloride (0.2 mL, 3 mmol). The mixture was slowly warmed to rt and stirred overnight. Then the mixture was cooled to 0° C. and methanol (2 mL) was slowly added. The mixture was stirred at rt for 3 h and then washed with aq. Na2CO3 solution, brine, dried (Na2SO4), and concentrated. The residue was purified via flash chromatography to afford the desired product as a white solid. 1H NMR (CDCl3, 400 MHz): 7.76 (t, J=1.6 Hz, 1H), 7.49 (t, J=1.3 Hz, 1H), 7.24 (t, J=2.2 Hz, 1H), 3.92 (s, 3H), 3.84 (s, 3H).

Provenance & Evidence