Novel synthesis of desymmetrized resorcinol derivatives: aryl fluoride displacement on deactivated substrates.
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.
Synthetic Chemistry, Chemical Development, GlaxoSmithKline, Five Moore Drive, P.O. Box 13398, Research Triangle Park, North Carolina 27709, USA.
Aujin
A
Kim
Jeremiah D
JD
Powers
Jennifer F
JF
Toczko
D002396:Catechols / Q000138:chemical synthesis; D005459:Fluorides / Q000737:chemistry; D005464:Fluorobenzenes / Q000737:chemistry; D012118:Resorcinols / Q000138:chemical synthesis* / Q000737:chemistry
D002396:Catechols; D005464:Fluorobenzenes; D012118:Resorcinols; C081153:1,2-difluorobenzene; C079487:1,3-difluorobenzene; D005459:Fluorides; C031389:resorcinol