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Synthesis of 4,6-Dichloro- and 4,6-Difluorophthalides: a Systematic Study on the Lithiation of 3,5-Dihalo-N,N-diisopropylbenzamides

✍ Scribed by Balázs Molnár; Gyula Simig; Balázs Volk

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
562 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

By taking advantage of the N,N‐diisopropylcarbamoyl moiety as a versatile ortho‐directing lithiation group, the preparation of 4,6‐dichloro‐ and 4,6‐difluorophthalides, starting from the corresponding 3,5‐dihalo‐N,N‐diisopropylbenzamides, is described here. The role of the lithiating agent, the formation of kinetically and thermodynamically favored products, and the marked difference between the dichloro and difluoro derivatives are discussed in detail.

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