Skip to main content
SpringerLink
Log in

An efficient approach to the synthesis of 2,3,4,5-tetrafluorophenol

  • Brief Communication
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new method for the preparation of 2,3,4,5-tetrafluorophenol from 2-[(2,3,4,5,6-pentafluorophenyl)thio]acetic acid has been proposed. It included the intramolecular cyclization of the salt of this acid in the presence of K2CO3 with the substitution of the ortho fluorine atom and the formation of a lactone, which under the reaction conditions underwent the ring-opening with the formation of the potassium salt of 2-[6-hydroxy(2,3,4,5-tetrafluorophenyl)-thio]acetic acid. The resulting salt was converted into methyl ester and desulfurized with Raney nickel to 2,3,4,5-tetrafluorophenol. The proposed method is a simple and efficient way to obtain poorly available 2,3,4,5-tetrafluorophenol in ∼58% total yield based on 2-[(2,3,4,5,6-pentafluorophenyl)thio]acetic acid.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. R. D. Chambers, Fluorine in Organic Chemistry, Blackwell Publishing Ltd., Oxford, 2004.

    Book  Google Scholar 

  2. K. Uneyama, Organo fluorine Chemistry, Blackwell Publishing Ltd., Oxford, 2006.

    Google Scholar 

  3. V. Prakash Reddy, Organo fluorine Chemistry in Biology and Medicine, Elsevier, Amsterdam, Netherlands, 2015.

    Google Scholar 

  4. A. Harsanyi, G. Sandford, Green Chem., 2015, 17, 2081–2086; DOI: https://doi.org/10.1039/C4GC02166E.

    Article  CAS  Google Scholar 

  5. L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul’shin, A. S. Vinogradov, Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, Russ. Chem. Rev., 2019, 88, 425–569; DOI: https://doi.org/10.1070/RCR4871.

    Article  CAS  Google Scholar 

  6. G. A. Selivanova, E. V. Tretyakov, Russ. Chem. Bull., 2020, 69, 838–858; DOI: https://doi.org/10.1007/s11172-020-2842-3.

    Article  CAS  Google Scholar 

  7. V. Romanov, E. Tretyakov, G. Selivanova, J. Li, I. Bagryanskaya, A. Makarov, D. Luneau, Crystals, 2020, 10, 786; DOI: https://doi.org/10.3390/cryst10090786.

    Article  CAS  Google Scholar 

  8. H. V. Volchkov, M. B. Lipkind, O. M. Nefedov, Russ. Chem. Bull., 2020, 69, 68–75; DOI: https://doi.org/10.1007/s11172-020-2724-8.

    Article  CAS  Google Scholar 

  9. E. V. Tretyakov, T. V. Makhneva, L. V. Politanskaya, I. Yu. Bagryanskaya, D. V. Stass, J. Struct. Chem., 2018, 59, 689–696; DOI: https://doi.org/10.1134/S0022476618030289.

    Article  CAS  Google Scholar 

  10. G. M. Brooke, B. S. Furniss, W. K. R. Musgrave, M. A. Quasem, Tetrahedron Lett., 1965, 34, 2991–2993; DOI: https://doi.org/10.1016/S0040-4039(01)89247-9.

    Article  Google Scholar 

  11. G. M. Brooke, B. S. Furniss, J. Chem. Soc., C, 1967, 869–873; DOI: https://doi.org/10.1039/J39670000869.

  12. K. Sung, R. J. Lagow, J. Mater. Chem., 1996, 6, 917–918; DOI: https://doi.org/10.1039/JM9960600917.

    Article  CAS  Google Scholar 

  13. L. Politanskaya, N. Troshkova, E. Tretyakov, Ch. Xi, J. Fluor. Chem., 2019, 227, 109371; DOI: https://doi.org/10.1016/j.jfluchem.2019.109371.

    Article  CAS  Google Scholar 

  14. Pat. RF 2536872 (in Russian).

  15. A. K. Petrov, B. V. Makarov, G. G. Yakobson, Dokl. Akad. Nauk SSSR [Dokl. Chem.], 1968, 179, 356–357 (in Russian).

    CAS  Google Scholar 

  16. I. V. Shchur, E. V. Shchegolkov, Y. V. Burgart, G. A. Triandafilova, V. V. Maslova, S. Y. Solodnikov, O. P. Krasnykh, S. S. Borisevich, S. L. Khursan, V. I. Saloutin, Chemistry Select, 2019, 4, 1483–1490; DOI: https://doi.org/10.1002/slct.201803523.

    CAS  Google Scholar 

  17. Pat. CN105384603A.

  18. I. T. Bazyl’, S. P. Kisil’, Y. V. Burgart, V. I. Saloutin, O. N. Chupakhin, J. Fluor. Chem., 1999, 94, 11–13; DOI: https://doi.org/10.1016/S0022-1139(98)00316-9.

    Article  Google Scholar 

  19. B. Boutevin, A. Rousseau, D. Bosc, J. Polym. Sci. Part. A: Polym. Chem., 1992, 30, 1279–1286; DOI: https://doi.org/10.1002/pola.1992.080300705.

    Article  CAS  Google Scholar 

  20. US Pat. 7262169.

  21. J. Grugier, J. Xie, I. Duarte, J.-M. Valéry, J. Org. Chem., 2000, 65, 979–984; DOI: https://doi.org/10.1021/jo991206p.

    Article  CAS  Google Scholar 

  22. F. A. R. Kaul, G. T. Puchta, H. Schneider, M. Grosche, D. Mihalios, W. A. Herrmann, J. Organomet. Chem., 2001, 621, 184–189; DOI: https://doi.org/10.1016/S0022-328X(00)00861-5.

    Article  CAS  Google Scholar 

  23. D. J. Abraham, P. E. Kennedy, A. S. Mehanna, D. C. Patwa, F. L. Williams, J. Med. Chem., 1984, 27, 967–978; DOI: https://doi.org/10.1021/jm00374a006.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    E. V. Tretyakov

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentreva, 630090, Novosibirsk, Russian Federation

    A. M. Maksimov, P. V. Nikul’shin & T. V. Mezhenkova

Authors
  1. E. V. Tretyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. M. Maksimov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. V. Nikul’shin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. V. Mezhenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Tretyakov.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 995–998, May, 2021.

The work was carried out in the framework of the Russian state assignment AAAA-A21-121011490017-5 for N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences. The authors of the work are grateful to the Chemical Service Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences for carrying out spectral and analytical measurements.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tretyakov, E.V., Maksimov, A.M., Nikul’shin, P.V. et al. An efficient approach to the synthesis of 2,3,4,5-tetrafluorophenol. Russ Chem Bull 70, 995–998 (2021). https://doi.org/10.1007/s11172-021-3178-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3178-3

Key words

Search

Navigation