Acetyl chloride → Methyl 4-bromo-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

Acetyl chloride (199 mL, 2.79 mol) is added to a solution of 4-bromo-2-methylbenzoic acid (500 g, 2.32 mol) in methanol (2500 mL) at 5° C. The mixture is heated at 65° C. for 7 hours. The mixture is cooled to room temperature and sodium carbonate (19 g, 0.18 mol) is added. The reaction mixture is stirred for 15 minutes. The slurry is filtered and the filtrate is concentrated under reduced pressure. The resulting residue is partitioned between MTBE (400 mL) and water (400 mL). The organic phase is washed with brine, dried over magnesium sulfate, and concentrated to give the title compound (520 g) as a golden oil. ES/MS m/e 216 (M+1).

Provenance & Evidence