Acetyl chloride → Methyl 4-Bromo-2-chlorobenzoate

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Reaction Steps

To anhydrous methanol (45 mL) was added acetyl chloride (1.9 mL) over 2 min. The mixture, which became slightly exothermic and evolved gas, was stirred for 15 min. 4-Bromo-2-chlorobenzoic acid (3.0 g) was added in one portion and the mixture was heated at gentle reflux for 16 h. The mixture was allowed to cool to room temperature and the solvent was removed with a rotary evaporator. The residue was partitioned between saturated aqueous sodium bicarbonate and diethyl ether. The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford the title compound as a white solid (2.89 g).

Provenance & Evidence