Trifluoroacetic acid → 4-Benzylbenzyl bromide

Participants

Reaction Steps

4-Benzoylbenzyl bromide (2.75 grams, 10.0 mmole) and triethylsilane (2.33 grams, 20 mmole) in trifluoroacetic acid (4.56 grams, 40 mmole) were warmed to 60° C. for 18 hours. The cooled mixture was diluted with ethyl acetate (50 ml) and carefully washed with saturated sodium bicarbonate solution (2×50 ml). After drying with magnesium sulfate, the extract was filtered and concentrated. The residue was chromatographed (0.5:99.5 to 2:98--ethyl acetate:hexane) to give 1.37 grams (52%) of 4-benzylbenzyl bromide as a colorless oil.

Provenance & Evidence