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Synthesis 2008(24): 4028-4032  
DOI: 10.1055/s-0028-1083246
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Straightforward Transformation of Pentafluorobenzaldehyde into 4-Aryloxy-2,3,5,6-tetrafluorobenzaldehydes

Daniel T. Gryko*, Dagmara Wyrostek, Agnieszka Nowak-Król, Katarzyna Abramczyk, Maciej K. Rogacki
Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: daniel@icho.edu.pl;
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Publication History

Received 21 August 2008
Publication Date:
01 December 2008 (online)

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Abstract

A new and practical process leading to 4-aryloxy-2,3,5,6-tetrafluorobenzaldehydes has been developed. The title skeleton is assembled in a convergent fashion from phenols and pentafluorobenzaldehyde via a nucleophilic substitution in the presence of inorganic fluorides. Scope and limitation studies have been conducted, revealing that the methodology is diversity tolerant, facilitating the introduction of various aryl and heteroaryl substituents. Altogether, 12 aldehydes were prepared in 14-93% yield.

Key words

phenols - ethers - fluorine - nucleophilic aromatic substitution - aldehydes

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