Hydrogen Bromide → (5-Bromopentyl)benzene

Participants

Reaction Conditions

Reaction Steps

A solution of 416.7 ml (1.83 mol) 48% strength hydrobromic acid is mixed with 50 g (0.304 mol) of 5-phenylpentan-1-ol at 0° C. and stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After reaction is complete, the mixture is cooled to room temperature and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate solution and dried over sodium sulfate. After filtration, the filtrate is is concentrated to dryness. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane). 59.4 g (0.26 mol, 86% of theory) of a colorless liquid are obtained.

Provenance & Evidence