Bromoacetyl bromide → Oleyl bromoacetate

Participants

Reaction Conditions

Reaction Steps

A solution of bromoacetyl bromide (0.49 ml; 5.65 mmol) in tetrahydrofuran (12 ml) is added, at 0° C., to a mixture of oleyl alcohol (1.00 ml; 3.77 mmol) and diisopropylethylamine (0.88 g; 5.65 mmol) in tetrahydrofuran (38 ml). The mixture is stirred for 2 h at 0° C. and then for 1 h at room temperature; it is then washed with 1N hydrochloric acid solution (20 ml) which is extracted with ether (50 ml). The combined organic phases are washed with saturated sodium carbonate solution (20 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by chromatography on a column of silica gel (eluent: 99/1 hexane/ether) to give oleyl 2-bromoacetate (1.31 g; 89%) in the form of a colorless oil.

Provenance & Evidence