Synthesis of 4-fluorophenols from 4-tert-butylphenols and fluoride sources under oxidative conditions

A Bienvenu, A Barthelemy, S Boichut…

Index: Bienvenu, Antoine; Barthelemy, Audrey; Boichut, Sarah; Marquet, Bernard; Billard, Thierry; Langlois, Bernard R. Collection of Czechoslovak Chemical Communications, 2002 , vol. 67, # 10 p. 1467 - 1478

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Citation Number: 14

Abstract

Abstract 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. ...