3,5-Dimethylphenol → 2-Bromo-3,5-dimethylphenol

Participants

Reaction Steps

To a solution of 3,5-dimethylphenol (15.0 g, 123 mmol) in carbon disulfide (330 mL) was slowly added N-bromosuccinimide (21.9 g, 123 mmol) in several batches with ice-cooling, and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the precipitated crystals were filtered and then were washed with ethyl acetate-hexane (10:1). The solution was concentrated, and the residue was purified by silica gel chromatography (ethyl acetate:hexane=1:9) to obtain 16.3 g (yield 66%) of the title compound. Oily matter.

Provenance & Evidence