Manufacturing synthesis of 5-substituted phthalides

Ferenc Faigl, Angelika Thurner, Balázs Molnár, Gyula Simig, Balázs Volk

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

A manufacturing synthesis of 5-chlorophthalide has been elaborated. The key step of the procedure is ortho-lithiation of 4-chloro-N,N-diisopropylbenzamide, followed by formylation with dimethyl formamide. Reduction of the formyl moiety and subsequent ring closure, which can be carried out also in one pot, led to 5-chlorophthalide in high overall yield. The procedure has also been successfully adapted for the synthesis of the 5-fluoro and 5-trifluoromethyl analogues. The compounds thus obtained are useful building blocks in the synthesis of various heterocyclic ring systems.

Original languageEnglish
Pages (from-to)617-622
Number of pages6
JournalOrganic Process Research and Development
Volume14
Issue number3
DOIs
Publication statusPublished - May 21 2010

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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