3-Bromothiophene → HCID 54264487, compound

Participants

Reaction Steps

3-Thienyl lithium was generated from 3-bromothiophene and n-butyl lithium at -70° C. To the 3-thienyl lithium was then added an excess of 1-chloro-4-iodobutane at dry ice-acetone temperature. Upon slow warm up to room temperature a mixture of 2 and 3-thienyl butylchloride were obtained. The mixture was converted to the 2- and 3-thienyl butyl amines via the azide intermediates (Scheme 9) as described for the synthesis of 2-thienyl butyl amine, then reacted with thiophosgene to give the desired product, 3-TBITC, in low yield. The 2 isomers were separated by preparative liquid chromatography using a recycling mode. The 3-TBITC was obtained in 97% purity.

Provenance & Evidence