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

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

doi:10.1021/jo00415a028

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 language	English (US)
Pages (from-to)	4115-4120
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	43
Issue number	21
DOIs	https://doi.org/10.1021/jo00415a028
State	Published - 1978

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Organic Chemistry

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title = "Synthesis of 3-Aryl-5-bromo-2(5H)-furanones",

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).",

author = "Edgar, {Mark T.} and George Pettit and Smith, {Thomas H.}",

year = "1978",

doi = "10.1021/jo00415a028",

language = "English (US)",

volume = "43",

pages = "4115--4120",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Synthesis of 3-Aryl-5-bromo-2(5H)-furanones

AU - Edgar, Mark T.

AU - Pettit, George

AU - Smith, Thomas H.

PY - 1978

Y1 - 1978

N2 - 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).

AB - 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).

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M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

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

Abstract

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