Boron tribromide → 1-(5-chloro-2-hydroxy-4-methyl-3-nitrophenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(5-chloro-2-methoxy-4-methyl-3-nitrophenyl)ethanone (8.9 g, 37 mmol, from Oakwood) in methylene chloride (200 mL) was added 1.0 M boron tribromide in methylene chloride (38.4 mL, 38.4 mmol) at −78° C. After stirring at −78° C. for 10 minutes, the reaction was allowed to warm up to 0° C., quenched with water at 0° C., and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. After evaporating to dryness under reduced pressure, the residue was used directly in next step (8.2 g, 98%). LCMS calculated for C9H9ClNO4 (M+H)+: m/z=230.0. found: 230.1.

Provenance & Evidence