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. 2017 Jun 9;22(6):966.
doi: 10.3390/molecules22060966.

Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity

Riadh Zriba  1 , Alaric Desmarchelier  2 , Frédéric Cadoret  3 , Sébastien Bouvet  4 , Anne-Laure Barthelemy  5 , Bruce Pégot  6 , Patrick Diter  7 , Guillaume Dagousset  8 , Jean-Claude Blazejewski  9 , Elsa Anselmi  10   11 , Yurii Yagupolskii  12 , Emmanuel Magnier  13
Affiliations

Dichlorotrifluoromethoxyacetic Acid: Preparation and Reactivity

Riadh Zriba et al. Molecules. .

Abstract

We describe the first gram scale preparation of the reagent dichlorotrifluoromethoxyacetic acid. This stable compound is obtained in five steps starting from the cheap diethylene glycol. The reactivity of the sodium salt of this fluorinated acid was also tested and allowed the preparation of new amides.

Keywords: amides; fluorine; trifluoromethoxy.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
First preparation of dichlorotrifluoromethoxyacetic acid 3.
Scheme 2
Scheme 2
Attempts at carbene generation.
Scheme 3
Scheme 3
Preparation of various dichlorotrifluoromethoxy acetamides.
See this image and copyright information in PMC

References

    1. Yagupolskii L.M. Synthesis of derivatives of phenyl trifluoromethyl ethers. Dokl. Acad. Nauk SSSR 1955, 105, 100–102. Chem. Abstr. 1956;50:11270b.
    1. Zeng Z., Gao T., Li Y., Wang X., Yang X., Wu M. Synthesis and biological activity of arylsulfonamide derivatives containing 2-arylamino-4(3H)-quinazolinone. J. Pest. Sci. 2016;41:171–174. doi: 10.1584/jpestics.D16-053. - DOI - PMC - PubMed
    1. Xu D., Guan J., Xu X., Gong S., Xu H. A New Method for the Synthesis of Oxadiazine Insecticide Indoxacarb. J. Heterocycl. Chem. 2016;63:1469–1473. doi: 10.1002/jhet.2449. - DOI
    1. Liu A., Wang X., Liu X., Li J., Chen H., Hu L., Yu W., He L., Liu W., Huang M. Synthesis and Fungicidal Activity of Novel 2-Heteroatomthiazole-based Carboxanilides. J. Heterocycl. Chem. 2017;54:1625–1629. doi: 10.1002/jhet.2668. - DOI
    1. Alverez C., Arkin M.R., Bulfer S.L., Colombo R., Kovaliov M., LaPorte M.G., Lim C., Liang M., Moore W.J., Neitz R.J., et al. Structure−Activity Study of Bioisosteric Trifluoromethyl and Pentafluorosulfanyl Indole Inhibitors of the AAA ATPase p97. ACS Med. Chem. Lett. 2015;6:1225–1230. doi: 10.1021/acsmedchemlett.5b00364. - DOI - PMC - PubMed

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