Phosphorus tribromide → 1-Bromo-4-phenylbutane

Participants

Reaction Steps

To 1.50 g of 4-phenylbutanol was added 385 μl of phosphorus tribromide with ice cooling, and the mixture was stirred at a room temperature for 5 minutes and then at 80° C. for one hour. To the reaction mixture were added 20 ml of ice water and 30 ml of ethyl acetate. The separated organic layer was, successively washed with water, 5% sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure to obtain an oily residue. The residue was applied to a silica gel column and eluted with hexane/benzene (6:1) to obtain 1.94 g of (4-bromobutyl)benzene as a colorless liquid.

Provenance & Evidence