1-Bromo-2-Chloroethane → 1-(2-Furyl)cyclopropanecarbonitrile

Participants

Reaction Steps

A solution of furan-2-acetonitrile (28.4 g) and 1-bromo-2-chloroethane (33.1 ml) in dimethyl sulphoxide (50 ml) was added slowly to a stirred suspenson of sodium hydride (60% dispersion in mineral oil ; 31.85 g) in dry dimethyl sulphoxide (300 ml) keeping the internal temperature just below 35° C. by occasional cooling. After stirring for 18 hours at ambient temperature the mixture was diluted with water (500 ml) and extracted with ether (1×200 then 2×100 ml). The combined extracts were dried over potassium carbonate and evaporated to an oil which was distilled at reduced pressure to give 1-(2-furyl)cyclopropanecarbonitrile (28.0 g) as a colourless oil, bp 54° C./0.55 mbar.

Provenance & Evidence