C3-Chlorination of C2-substituted benzo[<i>b</i>]thiophene derivatives in the presence of sodium hypochlorite.

ABSTRACT: Benzo[b]thiophene rings are common synthons for the development of novel drugs and materials, and thus, the discovery of facile ways for their functionalization is of value. In this work, a new method for the C3-chlorination of C2-substituted benzothiophene derivatives is described. The chlorine source is sodium hypochlorite pentahydrate (NaOCl·5H₂O), and optimal transformations occur in aqueous acetonitrile at 65-75 °C to provide the corresponding C3-halogenated products in variable yields (30-65%). The reaction occurs in the presence of vinyl and alkyl groups, while the presence of alcohols leads to competing oxidation reactions at the heterobenzylic position. The presence of a carbonyl group at the C2-position inhibited the halogenation reaction, while the use of benzo

SUBMITTER: Conrad Oppenheimer V 

PROVIDER: S-EPMC11484177 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature