Novel synthesis of desymmetrized resorcinol derivatives: aryl fluoride displacement on deactivated substrates

J Org Chem. 2006 Mar 3;71(5):2170-2. doi: 10.1021/jo0523868.

Abstract

A short, high-yielding synthesis of differentially substituted resorcinol derivatives has been developed that utilizes 1,3-difluorobenzene as the starting material and employs sequential nucleophilic aromatic substitution (S(N)Ar) reactions to generate desymmetrized products. The scope and limitations of the second S(N)Ar reaction on the deactivated 1-alkoxy-3-fluorobenzene intermediates have been investigated. This methodology has also been employed in the synthesis of desymmetrized catechol derivatives from 1,2-difluorobenzene.

MeSH terms

  • Catechols / chemical synthesis
  • Fluorides / chemistry
  • Fluorobenzenes / chemistry
  • Resorcinols / chemical synthesis*
  • Resorcinols / chemistry

Substances

  • Catechols
  • Fluorobenzenes
  • Resorcinols
  • 1,2-difluorobenzene
  • 1,3-difluorobenzene
  • Fluorides
  • resorcinol