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

doi:10.1135/CCCC20021467

Paper

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

Published 2002 · Antoine Bienvenu, A. Barthelemy, Sarah Boichut

Collection of Czechoslovak Chemical Communications

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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. When extended to 4-tert-butylacetanilide, this method delivers 4-fluoroacetanilide in a single step but in a modest yield.

Study Snapshot

This study demonstrates a two-step procedure for transforming 4-tert-Butylphenols into 4-fluorophenols under mild and safe conditions, with potential applications in organic synthesis and catalysis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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Citations

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