Dimethyl Sulfate → 3-Bromo-2,5-difluoro-4-methoxybenzaldehyde

Participants

Reaction Steps

To a solution of 3-bromo-2,5-difluoro-4-hydroxybenzaldehyde (48.4 g, 0.193 mmol) in DMF (200 mL) was added potassium carbonate (40.0 g) and dimethylsulfate (27.4 mL). The reaction mixture was stirred at room temperature overnight. The reaction was diluted wit ethylacetate and washed successively with water and brine, dried over magnesium sulfate, filtered and evaporated. The residue was triturated with hexane to afford 26 g of 3-bromo-2,5-difluoro-4-methoxy benzaldehyde. The mother liquor was evaporated and chromatographed on silica gel (0–10% ethyl acetate in hexane) to give 10.86 g of more product. (38% overall yield from 2,5-dinitrophenol).

Provenance & Evidence