Collect. Czech. Chem. Commun. 2002, 67, 1467-1478

Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions

Antoine Bienvenu, Audrey Barthelemy, Sarah Boichut, Bernard Marquet, Thierry Billard and Bernard R. Langlois*

Laboratoire SERCOF, UMR CNRS 5622, Université Claude Bernard-Lyon I, Bâtiment E. Chevreul, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne cedex, France


4-tert-Butylphenols can be easily transformed into 4-fluorophenols, provided that no coordinating moiety is present in 2-position, in a two step procedure under mild and safe conditions. The first step leads to 4-tert-butyl-4-fluorocyclohexa-2,5-dien-1-ones through an oxidative fluorination with [bis(trifluoroacetoxy)iodo]benzene and triethylamine tris(hydrofluoride), and is followed by an acid catalyzed aromatization with loss of isobutene. When extended to 4-tert-butylacetanilide, this method delivers 4-fluoroacetanilide in a single step but in a modest yield.

Keywords: Fluoroaromatics; Fluorinated compounds; 4-Fluorophenols; 4-tert-Butylphenols; 4-Fluoroacetanilide; 4-tert-Butylacetanilide; Oxidations; [Bis(trifluoroacetoxy)iodo]benzene; Triethylamine tris(hydrofluoride); Fluorinations.

References: 21 live references.