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Chlorination and decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid. Synthesis of 2-(dichloromethyl)- and 2-(difluoromethyl)heptafluoronaphthalenes

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Abstract

Decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid in DMF in the presence of NaHCO3 gave 2-methylheptafluoronaphthalene, and treatment with PCl5 on heating afforded dichloro(heptafluoronaphthalen-2-yl)acetic acid. Decarboxylation of the latter in DMF led to the formation of 2-(dichloromethyl)-heptafluoronaphthalene which was converted to 2-(difluoromethyl)heptafluoronaphthalene by heating with cesium fluoride.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    V. R. Sinyakov, T. V. Mezhenkova, V. M. Karpov & Ya. V. Zonov

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    Ya. V. Zonov

Authors
  1. V. R. Sinyakov
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  2. T. V. Mezhenkova
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  3. V. M. Karpov
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  4. Ya. V. Zonov
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Corresponding author

Correspondence to V. M. Karpov.

Additional information

Original Russian Text © V.R. Sinyakov, T.V. Mezhenkova, V.M. Karpov, Ya.V. Zonov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 10, pp. 1438–1441.

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Sinyakov, V.R., Mezhenkova, T.V., Karpov, V.M. et al. Chlorination and decarboxylation of (heptafluoronaphthalen-2-yl)acetic acid. Synthesis of 2-(dichloromethyl)- and 2-(difluoromethyl)heptafluoronaphthalenes. Russ J Org Chem 52, 1427–1431 (2016). https://doi.org/10.1134/S1070428016100092

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  • DOI: https://doi.org/10.1134/S1070428016100092

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