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

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Title:Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions
Creators:
Bienvenu, Antoine
Barthelemy, Audrey
Boichut, Sarah
Marquet, Bernard
Billard, Thierry
Langlois, Bernard R.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 10, pp. 1467-1478
Uncontrolled Keywords:4-Fluorophenols, Fluorinations, Oxidations, 4-<i>tert</i>-Butylacetanilide, [Bis(trifluoroacetoxy)iodo]benzene, 4-Fluoroacetanilide, Fluorinated compounds, Fluoroaromatics, Triethylamine tris(hydrofluoride), 4-<i>tert</i>-Butylphenols

Abstract

4-<i>tert</i>-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-<i>tert</i>-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-<i>tert</i>-butylacetanilide, this method delivers 4-fluoroacetanilide in a single step but in a modest yield. <p>

Title:Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions
Creators:
Bienvenu, Antoine
Barthelemy, Audrey
Boichut, Sarah
Marquet, Bernard
Billard, Thierry
Langlois, Bernard R.
Uncontrolled Keywords:4-Fluorophenols, Fluorinations, Oxidations, 4-<i>tert</i>-Butylacetanilide, [Bis(trifluoroacetoxy)iodo]benzene, 4-Fluoroacetanilide, Fluorinated compounds, Fluoroaromatics, Triethylamine tris(hydrofluoride), 4-<i>tert</i>-Butylphenols
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:10
Page Range:pp. 1467-1478
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021467UNSPECIFIED
ID Code:2007
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Bienvenu, Antoine; Barthelemy, Audrey; Boichut, Sarah; Marquet, Bernard; Billard, Thierry; Langlois, Bernard R. (2002) Synthesis of 4-Fluorophenols from 4-tert-Butylphenols and Fluoride Sources Under Oxidative Conditions. Collection of Czechoslovak Chemical Communications, 67 (10). pp. 1467-1478. ISSN 0010-0765

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