Carbon tetrabromide → 1-(Benzyloxy)-4-(2-bromoethyl)benzene

Participants

Reaction Steps

To a cooled (0° C.) solution of 3.00 g 4-benzyloxy phenethyl alcohol (13.1 mmol) in dichloromethane (132 mL) were added subsequently 5.17 g of triphenylphosphine (19.7 mmol) and 6.54 g carbon tetrabromide (19.7 mmol). The resulting mixture was stirred for 2 h at room temperature and was then evaporated. The residue was triturated with diethyl ether at −20° C. for 30 minutes, and then all solids were removed by filtration. and the filtrate was concentrated in vacuo. The residue was subjected to column chromatography on silica gel (1%→10% ethyl acetate in hexane) to give 2.80 g of the target compound (73% yield) as a pale yellow oil crystallizing upon standing.

Provenance & Evidence