Dimethyl Sulfate → 1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

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Reaction Steps

A mixture of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (10.0 g, 37.9 mmol), dimethyl sulfate (4.31 mL, 45.5 mmol) and potassium carbonate (10.5 g, 75.9 mmol) in acetone (200 mL) was heated at reflux overnight. After evaporation to dryness, the mixture was diluted with water, and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 20% EtOAc in hexane, to yield the desired product (8.8 g, 84%). LCMS calculated for C10H11BrClO2 (M+H)+: m/z=227.0. found: 277.0.

Provenance & Evidence