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Synthesis 2003(6): 0841-0844
DOI: 10.1055/s-2003-38683
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sodium Dithionite-Initiated Coupling of 1-Bromo-1-chloro-2,2,2-trifluoro­ethane with Pyrroles: A New, Convenient and Economical Synthesis of 5-(Trifluoromethyl)dipyrromethanes

Wojciech Dmowski*, Krystyna Piasecka-Maciejewska, Zofia Urbańczyk-Lipkowska
Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland
Fax: +48(22)6326681; e-Mail: dmowski@icho.edu.pl;
Further Information

Publication History

Received 31 January 2003
Publication Date:
16 April 2003 (online)

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Abstract

Sodium dithionite-initiated reactions of pyrrole and 1-methylpyrrole with 1-bromo-1-chloro-2,2,2-ethane in an acetonitrile-water mixture provide the respective 5-(trifluoromethyl)di­pyrromethanes 1 and 3 as main products in 40-58% isolated yields and of high purity. Small amounts of tripyrranes 2 and 4 are also formed and could be isolated from the reaction mixtures.

Key words

5-(trifluoromethyl)dipyrromethanes - pyrroles - 1-bromo-1-chloro-2,2,2-trifluoroethane - sodium dithionite

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Dmowski, W.; Ignatowska, J. J. Fluorine Chem., in press.