Some reactions of 7-chloro-3-methylbenzo[b]thiophen

Abstract

3-Bromomethyl-7-chlorobenzo[b]thiophen has been converted into related amino-, guanidino-, and ureido-compounds, among others, by modifications of known methods. Nitration, bromination, and acetylation of 7-chloro-3-methylbenzo[b]thiophen gave mainly the 2-substituted compounds. 7-Hydroxy- and 7-mercapto-3-methylbenzo[b]thiophen resulted from the treatment of the Grignard reagent derived from 7-chloro-3-methyl-benzo[b]thiophen with oxygen or with sulphur. Direct nucleophilic displacement of the 7-chloro-group also gave 7-hydroxy- or 7-amino-3-methylbenzo[b]thiophen in high yield.