Hydrogen Bromide → (5-Bromopentyl)benzene

Participants

Reaction Conditions

Reaction Steps

50 g (0.304 mol) of 5-phenylpentan-1-ol are added to a solution of 416.7 ml (1.83 mol) of 48% strength hydrobromic acid at 0° C., and the mixture is stirred at 0° C. for 30 min. The reaction solution is subsequently stirred at 10° C. for 12 hours. After reaction is complete, the mixture is cooled to room temperature and mixed with 200 ml of ethyl acetate. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulphate. After filtration, the filtrate is evaporated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 59.4 g (0.26 mol, 86% yield) of a colourless liquid are obtained.

Provenance & Evidence