What is the role of N-chlorosuccinimide (NCS) in comparison to sodium hypochlorite in the C3-chlorination of benzo[b]thiophene derivatives?

Label:chem

Topic
N-chlorosuccinimide is another chlorinating agent that can be used for the functionalization of benzo[b]thiophene derivatives.
Answer
N-chlorosuccinimide (NCS) can also achieve C3-chlorination of benzo[b]thiophene derivatives, yielding comparable results to sodium hypochlorite. However, NCS tends to result in competing vinyl halogenation when used with olefins, whereas sodium hypochlorite can selectively chlorinate the aromatic ring in the presence of olefins.
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