Home Chemistry Heterocyclic Building Blocks Benzofurans Benzofuran-2(3H)-One
Electrophilic Aromatic Substitution (EAS): Benzofuran-2(3H)-one, like benzene, can undergo EAS reactions. This involves the substitution of a hydrogen atom with an electrophile. The ketone oxygen and the positions on the furan and benzene rings are potential sites for electrophilic attack.
Nucleophilic Addition to the Carbonyl Group: The ketone functional group is susceptible to nucleophilic attack. This can lead to the formation of a variety of products, depending on the nature of the nucleophile.
Reduction of the Carbonyl Group: The ketone group can be reduced to a secondary alcohol using reducing agents like sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4).
Base-Catalyzed Reactions: The presence of a ketone group makes it susceptible to base-catalyzed reactions, such as aldol condensation or Claisen condensation.
Oxidation of the Benzofuran Ring: The benzofuran ring can be oxidized using strong oxidizing agents. This might lead to the formation of various functional groups depending on the conditions.
Substitution Reactions at Furan Ring: The furan ring is susceptible to nucleophilic and electrophilic substitution reactions. For example, it can undergo reactions with Grignard reagents or nucleophiles.
Cyclization Reactions: Depending on the conditions and reagents, benzofuran-2(3H)-one can participate in intramolecular reactions, leading to the formation of cyclic compounds.
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