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Synthesis 2005(11): 1771-1774  
DOI: 10.1055/s-2005-865336
PAPER
© Georg Thieme Verlag Stuttgart · New York

Practical and Efficient Synthesis of Tris(4-formylphenyl)amine, a Key Building Block in Materials Chemistry

Thomas Mallegol, Said Gmouh, Mohamed Aït Amer Meziane, Mireille Blanchard-Desce, Olivier Mongin*
Synthèse et ElectroSynthèse Organiques (CNRS, UMR 6510), Université de Rennes 1, Campus de Beaulieu, Bât. 10A, 35042 Rennes Cedex, France
Fax: +33(1)223236955; e-Mail: olivier.mongin@univ-rennes1.fr;
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Publication History

Received 26 January 2005
Publication Date:
25 April 2005 (online)

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Abstract

A short, practical and efficient preparation of tris(4-formylphenyl)amine, a key building block in materials chemistry, is described. It involves a two-flask synthesis from triphenylamine, which requires shorter overall time than the direct one-flask threefold Vilsmeier-Haack formylation, while giving higher yields. The reaction levels off at the disubstitution stage, due to the deactivation of the bis-iminium intermediate, but hydrolysis of the latter into a less deactivated dialdehyde allows the third formylation to occur. The simple experimental protocol makes this method more convenient than the previously reported procedures.

Key words

materials chemistry - building block - aldehydes - electrophilic aromatic substitutions - Vilsmeier-Haack reaction

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25

This could explain why DMF is often used in larger amounts than POCl3.24 To overcome this problem, other authors tried to use high boiling chlorinated solvents, such as 1,2-dichloroethane, but the yields remained low.19,26