1612240-35-3

Upstream product

• 53783-59-8 (E)-2-phenyl-but-2-en-1-ol 
• 1612240-13-7 (E)-1-chloro-3-((2-phenylbut-2-en-1-yl)oxy)benzene 
• 675825-21-5 Lithium enolate of the acetaldehyde 

Downstream Products

• 1612240-42-2 (E)-5-((2-phenylbut-2-en-1-yl)oxy)bicyclo[4.2.0]octa-1,3,5-trien-7-one 

Relevant academic research and scientific papers

Concise synthesis of functionalized benzocyclobutenones

A concise approach to access functionalized benzocyclobutenones from 3-halophenol derivatives is described. This modified synthesis employs a [2+2] cycloaddition between benzynes generated from dehydrohalogenation of aryl halides using LiTMP and acetaldehyde enolate generated from n-BuLi and THF, followed by oxidation of the benzocyclobutenol intermediates to provide benzocyclobutenones. The [2+2] reaction can be run on a 10-g scale with an increased yield. A number of functional groups including alkenes and alkynes are tolerated. Coupling of benzynes with ketene silyl acetals to give 8-substituted benzocyclobutenones is also demonstrated.