Synthesis of 3-Aryl-5-bromo-2(5H)-furanones

Mark T. Edgar, George Pettit, Thomas H. Smith

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Abstract

A synethetic route to 3-aryl-5-bromo-2(5H)-furanones (7) based on treating a methyl 2-aryl-4-oxobutyrate (5) with bromine in acetic acid has been developed. The methyl 2-aryl-4-oxobutyrates were prepared in high yield by the following sequence: alkylation of an arylacetic acid using lithium diisopropylamide and allyl bromide, esterification with diazomethane to yield a methyl 2-aryl-4-pentenoate (4), and ozonolysis (4 → 5).

Original languageEnglish (US)
Pages (from-to)4115-4120
Number of pages6
JournalJournal of Organic Chemistry
Volume43
Issue number21
DOIs
StatePublished - Jan 1 1978

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ASJC Scopus subject areas

  • Organic Chemistry

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