Hydrochloric Acid → 1-(1-Benzothiophen-2-yl)cyclobutane-1-carbonitrile

Participants

Reaction Steps

A solution of benzo[b]thiophen-2-acetonitrile (8.05 g) and 1,3-dibromopropane (5.2 ml) in ether (50 ml) was added dropwise under nitrogen over 1 hour to a stirred, ice-cold suspension of finely-powdered potassium hydroxide (13.53 g) in dimethyl sulphoxide (100 ml). When the addition was complete, the mixture was stirred at ambient temperature for 4 hours, then it was added to ice-cold water (200 ml). The resulting mixture was acidified to pH4 by the addition of concentrated hydrochloric acid, then the product was extracted into ether (3×200 ml). The combined extracts were washed with water (500 ml), dried (MgSO4), and the solvent was removed in vacuo to give 1-(benzo[b]thiophen-2-yl)cyclobutanecarbonitrile as a red oil (8.16 g) which was used without purification.

Provenance & Evidence