Hydrogen Bromide → (5-Bromopentyl)benzene

Participants

Reaction Conditions

Reaction Steps

At 0° C., 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, and the mixture is stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After the reaction has gone to completion, 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 and dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane). This gives 59.4 g (0.26 mol, 86% of theory) of a colorless liquid.

Provenance & Evidence