Reaction of methyl 2,3-pentadienoate with bromine. Preparation of 4-bromo-5-methyl-5H-furan-2-one

J. Font, A. Gracia, P. de March

Research output: Contribution to journalArticleResearchpeer-review

6 Citations (Scopus)

Abstract

Treatment of methyl 2,3-pentadlenoate, 3, with bromine in carbon tetrachloride affords a complex mixture, whose main products are methyl (E)- and (Z)-3,4-dlbromo-2-pentenoate, 9 and 10, and 4-bromo-5-methyl-5H-furan-2-one, 4. The mechanism of formation of these and other minor compounds is discussed. Hydrolysis of the crude mixture in the presence of barium hydroxide affords lactone 4 in 30% overall yield. © 1990.
Original languageEnglish
Pages (from-to)4407-4416
JournalTetrahedron
Volume46
Issue number12
DOIs
Publication statusPublished - 1 Jan 1990

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