Skip to main content
Log in

Synthesis of Bromochloropolyfluorobiphenyls Containing Bromine and Chlorine Atoms in the 4 and 4,4′ Positions

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

A new method for the synthesis of 4-chlorononafluoro- and 4-bromononafluorobiphenyl by the reactions of nonafluorobiphenyl-4-thiol with Cl2, PCl5, and Br2, as well as of 4,4′-dichlorooctafluorobiphenyl from octafluorobiphenyl-4,4′-dithiol, 4′-chlorooctafluorobiphenyl-4-thiol, Cl2, and PCl5 was developed. 4-Bromo-4′-chlorooctafluorobiphenyl was synthesized for the first time from 4′-chlorooctafluorobiphenyl-4-thiol and Br2. 4,4′-Dichlorooctafluorobiphenyl was obtained as the main product in the reaction of 4′-bromooctafluorobiphenyl-4-thiol with PCl5.

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

Access this article

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

Instant access to the full article PDF.

Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Vinogradov, A.S. and Platonov, V.E., Russ. J. Org. Chem., 2015, vol. 51, p. 1388. https://doi.org/10.1134/S107042801510005X

    Article  CAS  Google Scholar 

  2. Brooke, G.M., Chambers, R.D., Heyes, J., and Musgrave, W.K.R., J. Chem. Soc., 1964, p. 729. https://doi.org/10.1039/JR9640000729

  3. Yakobson, G.G., Shteingarts, V.D., Miroshnikov, A.I., and Vorozhtsov, N.N., Dokl. Akad. Nauk SSSR, 1964, vol. 159, no. 5, p. 1109.

    CAS  Google Scholar 

  4. Belf, L.J., Buxton, M.W., and Tilney-Bassett, J.F., Tetrahedron, 1967, vol. 23, p. 4719. https://doi.org/10.1016/S0040-4020(01)92570-0

    Article  CAS  Google Scholar 

  5. Chambers, R.D. and Spring, D.J., J. Chem. Soc. C, 1968, p. 2394. https://doi.org/10.1039/J39680002394

  6. Chambers, R.D., Fluorine in Organic Chemistry, Oxford: Blackwell, 2004.

  7. Callender, D.D., Coe, P.L., and Tatlow, J.C., Tetrahedron, 1966, vol. 22, no. 2, p. 419. https://doi.org/10.1016/0040-4020(66)80006-6

    Article  Google Scholar 

  8. Larionov, S.V., Myachina, L.I., Sheludyakova, L.A., Korol’kov, I.V., Rakhmanova, M.I., Plyusnin, P.E., Vinogradov, A.S., Karpov, V.M., Platonov, V.E., and Fadeeva, V.P., Russ. J. Gen. Chem., 2015, vol. 85, no. 7, p. 1617. https://doi.org/10.1134/S1070363215070075

    Article  CAS  Google Scholar 

  9. Cheplakova, A.M., Kovalenko, K.A., Samsonenko, D.G., Lazarenko, V.A., Khrustalev, V.N., Vinogradov, A.S., Karpov, V.M., Platonov, V.E., and Fedin, V.P., Dalton Trans., 2018, vol. 47, p. 3283. https://doi.org/10.1039/C7DT04566B

    Article  CAS  PubMed  Google Scholar 

  10. Cheplakova, A.M., Kovalenko, K.A., Vinogradov, A.S., Karpov, V.M., Platonov, V.E., and Fedin, V.P., J. Porous Mater., 2020, vol 27, p. 1773. https://doi.org/10.1007/s10934-020-00941-w

  11. Ivushkin, V.A., Sazonov, P.K., Artamkina, G.A., and Beletskaya, I.P., J. Organomet. Chem., 2000, vol. 597, nos. 1–2, p. 77. https://doi.org/10.1016/S0022-328X(99)00598-7

    Article  CAS  Google Scholar 

  12. Cohen, S.C and Massey, A.G., Chem. Commun., 1966, p. 457. https://doi.org/10.1039/C19660000457

  13. Cohen, S.C., Fenton, D.E., Shaw, D., and Massey, A.G., J. Organomet. Chem., 1967, vol. 8, no. 1, p. 1. https://doi.org/10.1016/S0022-328X(00)84697-5

    Article  CAS  Google Scholar 

  14. Filler, R., Fiebig, A.E., and Pelister, M.Y., J. Org. Chem., 1980, vol. 45, no. 7, p. 1290. https://doi.org/10.1021/jo01295a025

    Article  CAS  Google Scholar 

  15. Sakamoto, Y., Suzuki, T., Miura, A., Fujikawa, H., Tokito, S., and Taga, Y., J. Am. Chem. Soc., 2000, vol. 122, no. 8, p. 1832. https://doi.org/10.1021/ja994083z

    Article  CAS  Google Scholar 

  16. Rozhkov, A.V., Eliseeva, A.A., Baykov, S.V., Galmés, B., Frontera, A., and Kukushkin, V.Yu., Cryst. Growth Design, 2020, vol. 20, no. 9, p. 5908. https://doi.org/10.1021/acs.cgd.0c00606

    Article  CAS  Google Scholar 

  17. Senaweera, S. and Weaver, J.D., Chem. Commun., 2017, p. 7545. https://doi.org/10.1039/c7cc03996d

  18. Politanskaya, L.V., Selivanova, G.A., Panteleeva, E.V., Tret’yakov, E.V., Platonov, V.E., Nikul’shin, P.V., Vinogradov, A.S., Zonov, Ya.V., Karpov, V.M., Mezhenkova, T.V., Vasil’yev, A.V., Koldobskii, A.B., Shilova, O.S., Morozova, S.M., Burgart, Ya.V., Shchegolkov, E.V., Saloutin, V.I., Sokolov, V.B., Aksinenko, A.Yu., Nenaidenko, V.G., Moskalik, M.Yu., Astakhova, V.V., Shainyan, B.A., Tabolin, A.A., Ioffe, S.L., Muzalevskii, V.M., Balenkova, E.S., Shastin, A.V., Tyutyunov, A.A., Boiko, V.E., Igumnov, S.M., Dilman, A.D., Adonin, N.Yu., Bardin, V.V., Masoud, S.M., Vorob’yeva, D.V., Osipov, S.N., Nosova, E.V., Lipunova, G.N., Charushin, V.N., Prima, D.O., Makarov, A.G., Zibarev, A.V., Trofimov, B.A., Sobenina, L.N., Belyaeva, K.V., Sosnovskikh, V.Y., Obydennov, D.L., and Usachev S.A., Russ. Chem. Rev., 2019, vol. 88, no. 5, p. 425. https://doi.org/10.1070/RCR4871

    Article  CAS  Google Scholar 

  19. Holland, D.G., Moore, G.J., and Tamborski, C., J. Org. Chem., 1964, vol. 29,no. 6, p. 1562. https://doi.org/10.1021/jo01029a069

    Article  CAS  Google Scholar 

  20. Holland, D.G., Moore, G.J., and Tamborski, C., Chem. Ind., 1965, p. 1376.

  21. Gouverneur, P. and Soumillion, J.P., Tetrahedron Lett., 1976, vol. 17, no. 2, p. 133. https://doi.org/10.1016/S0040-4039(00)93040-5

    Article  Google Scholar 

  22. Traynham, J.G., Tetrahedron Lett., 1976, vol. 17, no. 26, p. 2213. https://doi.org/10.1016/00404039(76)80031-7

    Article  Google Scholar 

  23. Langille, K. and Peach, M.E., Can. J. Chem., 1970, vol. 48, no. 9, p. 1475. https://doi.org/10.1139/v70-241

    Article  Google Scholar 

  24. March, J., Advanced Organic Chemistry, New York: Wiley-Interscience, 1985.

  25. Sheppard, W.A. and Taft, R.W., J. Am. Chem. Soc., 1972, vol 94, no. 6, p. 1919. https://doi.org/10.1021/ja00761a022

    Article  Google Scholar 

  26. Sheppard, W.A. and Sharts, C.M., Organic Fluorine Chemistry, New York: W.A. Benjamin, 1969.

  27. Goerner, G.L. and Nametz, R.C., J. Am. Chem. Soc., 1951, vol 73, no. 6, p. 2940. https://doi.org/10.1021/ja01150a509

    Article  Google Scholar 

  28. Neil, R.J. and Peach, M.E., J. Fluorine Chem., 1971/72, vol. 1, p. 257. https://doi.org/10.1016/S0022-1139(00)83223-6

    Article  Google Scholar 

  29. Pushkina, L.N., Stepanov, A.P., Zhukov, V.S., and Naumov, A.D., Zh. Org. Khim., 1972, vol. 8,no. 3, p. 586.

    CAS  Google Scholar 

  30. Patent GB 1135773, 1968; Chem. Abstr. A, 1969, vol. 70, p. 57415.

  31. Artamkina, G.A., Sazonov, P.K., Ivushkin, V.A., and Beletskaya, I.P., Chem. Eur. J., 1998, vol 4, no. 7, p. 1169. https://doi.org/10.1002/(SICI)1521-3765(19980710)4:

    Article  Google Scholar 

  32. Cohen, S.C., Fenton, D.E., Tomlinson, A.J., and Massey, A.G., J. Organomet. Chem., 1966, vol. 6, no. 4, p. 301. https://doi.org/10.1016/S0022-328X(00)81508-9

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are grateful to the Chemical Research Center for Collective Use, Siberian Branch, Russian Academy of Sciences, for spectral and analytical measurements.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. E. Platonov.

Ethics declarations

No conflict of interest was declared by the authors.

Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 7, pp. 1049–1058 https://doi.org/10.31857/S0044460X2107009X.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikul’shin, P.V., Maksimov, A.M. & Platonov, V.E. Synthesis of Bromochloropolyfluorobiphenyls Containing Bromine and Chlorine Atoms in the 4 and 4,4′ Positions. Russ J Gen Chem 91, 1316–1324 (2021). https://doi.org/10.1134/S1070363221070097

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221070097

Keywords:

Navigation