What is the role of sodium hypochlorite pentahydrate (NaOCl·5H2O) in the C3-chlorination of C2-substituted benzo[b]thiophene derivatives?

Label:chem

Topic
Sodium hypochlorite pentahydrate is used as a chlorine source in the C3-chlorination of C2-substituted benzo[b]thiophene derivatives, facilitating the functionalization of these heterocyclic compounds.
Answer
Sodium hypochlorite pentahydrate acts as an efficient chlorinating agent, enabling the C3-chlorination of benzo[b]thiophene derivatives under mild conditions (65–75°C in aqueous acetonitrile). It forms a hypochlorous acidium ion that generates a chloronium ion intermediate, leading to the formation of C3-chlorinated products.
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