A selective synthesis of 4-bromo-2-furancarboxaldehyde and its pinacolborane derivative

✍ Scribed by Ohad Ilovich; Joseph Deutsch

• Book ID: 102344930
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2005
• Tongue: English
• Weight: 48 KB
• Volume: 42
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570420723

✦ Synopsis

A selective synthesis of ethylene acetal of 4-bromo-2-furancarboxaldehyde (4) and its pinacolborane derivative (5) is described. The synthesis was carried out using 2-furancarboxaldehyde (1) that was brominated to 4,5-dibromo-2-furancarboxaldehyde (2) in an emulsion of aluminum chloride and methylene chloride. The product was isolated, protected as ethylene acetal, and selectively debrominated to the ethylene acetal of 4-bromo-2-furancarboxaldehyde (4) in one step. This moiety was reacted with pinacolborane to give a reactive reagent of Suzuki coupling.