Russian Journal of Organic Chemistry

, Volume 52, Issue 10, pp 1427–1431 | Cite as

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

  • V. R. Sinyakov
  • T. V. Mezhenkova
  • V. M. Karpov
  • Ya. V. Zonov


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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Vlasov, V.M. and Yakobson, G.G., J. Org. Chem. USSR, 1976, vol. 12, p. 2345.Google Scholar
  2. 2.
    Sinyakov, V.R., Zonov, Ya.V., Karpov, V.M., Beregovaya, I.V., and Platonov, V.E., Russ. J. Org. Chem., 2013, vol. 49, p. 1010.CrossRefGoogle Scholar
  3. 3.
    Pozdnyakovich, Yu.V. and Shteingarts, V.D., J. Fluorine Chem., 1974, vol. 4, p. 283; ibid., p. 297.CrossRefGoogle Scholar
  4. 4.
    Fadeev, D.S., Chuikov, I.P., and Mamatyuk, V.I., J. Fluorine Chem., 2016, vol. 182, p. 53.CrossRefGoogle Scholar
  5. 5.
    Burdon, J. and Rimmington, T.W., J. Fluorine Chem., 1985, vol. 27, p. 257.CrossRefGoogle Scholar
  6. 6.
    Klimenko, L.S., Karpov, V.M., Platonov, V.E., and Yakobson, G.G., J. Org. Chem. USSR, 1979, vol. 15, p. 130.Google Scholar
  7. 7.
    Gething, B., Patrick, C.R., Smith, B.J.K., and Tatlow, J.C., J. Chem. Soc., 1962, p. 190.Google Scholar
  8. 8.
    Shteingarts, V.D., Osina, O.I., Kostina, N.G., and Yakobson, G.G., Zh. Org. Khim., 1970, vol. 6, p. 833.Google Scholar
  9. 9.
    Weigert, F.J., J. Fluorine Chem., 1993, vol. 61, p. 1.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • V. R. Sinyakov
    • 1
  • T. V. Mezhenkova
    • 1
  • V. M. Karpov
    • 1
  • Ya. V. Zonov
    • 1
    • 2
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia

Personalised recommendations