3,5-Dimethylphenol → 2-BroMo-3,5-diMethylphenol

Participants

Reaction Steps

N-bromosuccinimide (178 g, 1.00 mmol) was slowly added to a solution of toluene (1.0 L) containing 3,5-dimethylphenol (122 g, 1.00 mol) under ice-cooling condition, and then the mixture was warmed to room temperature and stirred for 2 hours. The mixture was concentrated under reduced pressure, and then the residue was suspended in hexane (400 mL) to remove insolubles by filtration. The filtrate was concentrated, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate 9:1) to give 61.6 g of the title compound (yield: 31%).

Provenance & Evidence