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

✍ Scribed by J. Font; A. Gracia; P. de March

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 554 KB
Volume: 46
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86775-2

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✦ Synopsis

Treatment of methyl 2,3-pentadienoate, 3, with bromine in carbon tetrachloride affords a complex mixture. whose main products are methyl (g)-and fZ)-3,4-dibromo-2-pentenoate, 9 and 10, and I-bromo-5methyl-5E-furan-2zone, 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.

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