What is the effect of benzofuran on the C3-chlorination reaction when used in place of benzo[b]thiophene?

Label:chem

Topic
The C3-chlorination reaction is specific to benzo[b]thiophene derivatives, and the presence of other heterocyclic compounds can alter the reaction outcome.
Answer
When benzofuran is used instead of benzo[b]thiophene, the reaction becomes highly exothermic and leads to the formation of unidentified byproducts, presumably via a peroxide intermediate. This indicates that the heteroatom (sulfur in benzo[b]thiophene) plays a crucial role in facilitating the chlorination reaction.
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