4-Bromobutyronitrile → 5-benzyl-3,4-dihydro-2H-pyrrole

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Reaction Steps

To a solution of 4-bromobutyronitrile (2.0 g, 13.5 mmol) in toluene (70 ml) was added 1.0 M benzylmagnesium bromide (20.0 ml, 20.0 mmol) in diethyl ether (70 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was partitioned between 0.1N hydrochloric acid and ethyl acetate, and the organic layer was washed with aqueous sodium hydrogen carbonate, dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford 5-benzyl-3,4-dihydro-2H-pyrrole (2.85 g). This compound was used without further purification.

Provenance & Evidence