Journal of Organic Chemistry 2006-03-03

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

Aujin Kim, Jeremiah D Powers, Jennifer F Toczko

Index: J. Org. Chem. 71(5) , 2170-2, (2006)

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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.