Quinoline → 4-Chloro-1-benzothiophene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-carboxy-4-chlorobenzo[b]thiophene (7.24 g), quinoline (36 ml), and copper powder (1.45 g) was stirred at 145 to 155° C. for 1 hour. After the mixture was allowed to cool to room temperature, the mixture was diluted with diisopropyl ether (145 ml), and insoluble materials were removed by filtration. The filtrate was washed with dilute hydrochloric acid (40 ml of 35% concentrated hydrochloric acid+200 ml of cold water) and with water, then dried over magnesium sulfate, and concentrated. A trace amount of precipitates was further removed from the concentrate by filtration to obtain 4-chlorobenzo[b]thiophene.

Provenance & Evidence