Water → 1-(Chloromethyl)cyclopentane-1-carbonitrile

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Reaction Steps

A solution of cyclopentanecarbonitrile (14.3 g, 150 mmol) in THF (25 ml) was added dropwise to a stirred solution of lithium diisopropylamide (158 mmol) in THF (150 ml) and hexane (100 ml), under dry nitrogen, keeping the temperature below -65°. After 0.5 h, the solution was warmed to ambient temperature and added to a stirred solution of bromochloromethane (49.4 ml, 750 mmol) in THF (50 ml) keeping the temperature below -65°. The solution was allowed to warm to ambient temperature and, after 18 h, poured into water (500 ml). The aqueous mixture was extracted with CHCl3 (3×250 ml). The extracts were washed with 2N HCl (100 ml) and H2O (100 ml), dried (MgSO4), and evaporated under reduced pressure to give an oil which was distilled to give a pale yellow oil (8.9 g) b.p. 96° at 10 mmHg.

Provenance & Evidence