Carbon tetrabromide → 5-Bromomethyl-4-chlorothiophene-3-carbonitrile

Participants

Reaction Steps

36.1 g (137 mmol) of triphenylphosphine were added at 5° C. to a solution of 21.7 g (125 mmol) of 5-hydroxymethyl-4-chlorothiophene-3-carbonitrile in 250 ml of tetrahydrofuran. Then, a solution of 45.6 g (137 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was stirred overnight at room temperature. The precipitate was filtered off, the filtrate was concentrated on a rotary evaporator under a water pump vacuum, and the residue was purified by column chromatography (eluant petroleum ether:dichloromethane 1:1). This gave 26.0 g (88%) of the title compound as an oil.

Provenance & Evidence