Acetone → Methyl 4-bromo-3-methoxybenzoate

Participants

Reaction Steps

To a solution of 4-bromo-3-hydroxybenzoic acid (14.480 mmol, 2.600 g) in acetone (180 mL), potassium carbonate (62.988 mmol, 8.710 g) and dimethylsulfate (31.422 mmol, 2.970 mL) were added. The reaction was stirred at RT for 30 minutes and evaporated to dryness. The residue was then diluted with water and extracted with ethyl acetate. The collected organic layer was washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. 4-Bromo-3-methoxy-benzoic acid methyl ester was isolated by chromatography on silica gel eluting with cyclohexane containing from 0% to 20% ethyl acetate. Yield: 47%.

Provenance & Evidence