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Synthesis 2010(2): 361-363  
DOI: 10.1055/s-0029-1217086
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© Georg Thieme Verlag Stuttgart ˙ New York

An Improved Procedure for the Preparation of [Bis(2,2,2-trifluoroethyl)phosphono]acetic Acid

Viviana da Silva Prado, Antonio Carlos B. Burtoloso*
Instituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brazil
Fax: +55(16)33739952; e-Mail: antonio@iqsc.usp.br;
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Publication History

Received 20 June 2009
Publication Date:
03 November 2009 (online)

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Abstract

A different and improved procedure for the preparation of [bis(2,2,2-trifluoroethyl)phosphono]acetic acid in just one step from bis(2,2,2-trifluoroethyl) phosphonate is described. The protocol employs a Michaelis-Becker reaction between commercially available bis(2,2,2-trifluoroethyl) phosphonate and bromoacetic acid, furnishing [bis(2,2,2-trifluoroethyl)phosphono]acetic acid in 50-54% yield.

Key words

[bis(2,2,2-trifluoroethyl)phosphono]acetic acid - Horner-Wadsworth-Emmons (HWE) reaction - Michaelis-Becker reaction - Still-Gennari reagents

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10

Recrystallized with hexanes. The solid was then dissolved in anhyd CHCl3 and the solvent removed under vacuum.