Hydrochloric Acid → 1-(3-Thienyl)cyclopropanecarbonitrile

Participants

Reaction Steps

A solution of thiophene-3-acetonitrile (30 g) and 1-bromo-2-chloroethane (40.8 ml) in dimethyl sulphoxide (120 ml) was added slowly dropwise to a well stirred suspension of sodium hydride (60% dispersion in mineral oil; 38.8 g) in dimethyl sulphoxide (800 ml) at 30°-35° C. The solution was stirred at ambient temperature for 21 hours then water (100 ml) was carefully added followed by hydrochloric acid (2M; 100 ml). The mixture was extracted with ether (6×80 ml) and the combined extracts washed with water (2×100 ml) then brine and then dried over magnesium sulphate. The solvent was removed in vacuo and the residue washed with petroleum ether (bp 60°-80° C.) before distillation under reduced pressure which gave 1-(3-thienyl)cyclopropanecarbonitrile as an oil (26.3 g), bp 82°-86° C./2 mbar.

Provenance & Evidence