Carbon Tetrachloride → 1-(Chloromethyl)-3,5-bis(trifluoromethyl)benzene

Participants

Reaction Steps

Triphenylphosphine (371 mg, 1.41 mmol) was added to a solution of 3,5-bistrifluoromethylbenzyl alcohol (257 mg, 1.05 mmol) in dry CCl4 (2 ml). The mixture was refluxed for 1 h, then cooled to room temp. Pentane (2 ml) was added, and the mixture stirred for a further 5 min., then filtered. The solid was washed with pentane (2 ml), and the filtrate concentrated in vacuo. The crude product was purified by column chromatography [SiO2: hexane-ethyl acetate 4:1] to give 3,5-bistrifluoromethylbenzyl chloride (162 mg, 59%); TLC (hexane-ethyl acetate 1:1) rf=0.73.

Provenance & Evidence