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FeBr2-catalyzed chlorination of aromatic compounds with ButOCl

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Abstract

A method for the FeBr2-catalyzed chlorination of alkyl and oxy derivatives of benzene with ButOCl has been developed. Chlorination of 4-nitrophenol gave 2-chloro-4-nitrophenol (nitrofungin) in 90 % yield.

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References

  1. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev., 2002, 102, 1359; DOI: https://doi.org/10.1021/cr000664r.

    Article  CAS  PubMed  Google Scholar 

  2. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem., Int. Ed., 2005, 44, 4442; DOI: https://doi.org/10.1002/anie.200500368.

    Article  CAS  Google Scholar 

  3. K. Smith, M. Butters, W. E. Paget, D. Goubet, E. Fromentin, B. Nay, Green Chem., 1999, 1, 83; DOI: https://doi.org/10.1039/A901395D.

    Article  CAS  Google Scholar 

  4. A. Paik, S. Paul, S. Bhowmik, R. Das, T. Naveen, S. Rana, Asian J. Org. Chem., 2022, 11, e202200060; DOI: https://doi.org/10.1002/ajoc.202200060.

    Article  CAS  Google Scholar 

  5. R. Das, M. Kapur, Asian J. Org. Chem., 2018, 7, 1524; DOI: https://doi.org/10.1002/ajoc.201800142.

    Article  CAS  Google Scholar 

  6. X. Liu, X. Zhao, F. Liang, B. Ren, Org. Biomol. Chem., 2018, 16, 886; DOI: https://doi.org/10.1039/C7OB03081A.

    Article  CAS  PubMed  Google Scholar 

  7. A. V. Kutchin, I. V. Fedorova, I. V. Loginova, I. Yu. Chukicheva, Russ. Chem. Bull., 2023, 72, 202; DOI: https://doi.org/10.1007/s11172-023-3725-1.

    Article  CAS  Google Scholar 

  8. R. I. Khusnutdinov, A. R. Bayguzina, U. M. Dzheilev, Organicheskie i Neorganicheskie Gipogalogenity v Organicheskom Sintese [Organic and Inorganic Hypohalides in Organic Synthesis’, Nauka, Moskva, 2016, 277 p. (in Russian).

    Google Scholar 

  9. A. R. Bayguzina, L. I. Gallyamova, L. M. Khalilov, R. I. Khusnutdinov, J. Fluorine Chem., 2019, 226, 109346; DOI: https://doi.org/10.1016/j.jfluchem.2019.109346.

    Article  CAS  Google Scholar 

  10. K. Shibatomi, Y. Zhang, H. Yamamoto, Chem.-Asian J., 2008, 3, 1581; DOI: https://doi.org/10.1002/asia.200800087.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Y. Zhang, K. Shibatomi, H. Yamamoto, Synlett, 2005, 18, 2837; DOI: https://doi.org/10.1055/s-2005-918919.

    Google Scholar 

  12. K. Smith, M. Butters, B. Nay, Synthesis, 1985, 12, 1157; DOI: https://doi.org/10.1055/s-1985-31462.

    Article  Google Scholar 

  13. H. Shaw, H. D. Perlmutter, C. Gu, S. D. Arco, T. O. Quibuyen, J. Org. Chem., 1997, 62, 236; DOI: https://doi.org/10.1021/jo950371b.

    Article  CAS  PubMed  Google Scholar 

  14. D. Ginsburg, J. Am. Chem. Soc., 1951, 73, 2723; DOI: https://doi.org/10.1021/ja01150a084.

    Article  Google Scholar 

  15. M. D. Mashkovsky, Lekarstvennye Sredstva [Drugs and Medicinal Preparations], Vol. 2, 14 ed., Novaya Volna, Moskva, 2002, p. 265. (in Russian)

    Google Scholar 

  16. A. A. Konarev, Russ. Chem. Bull., 2023, 72, 500; DOI: https://doi.org/10.1007/s11172-023-3813-4.

    Article  CAS  Google Scholar 

  17. M. J. Mintz, C. Walling, Org. Synth., 2003, 49, 9; DOI: https://doi.org/10.15227/orgsyn.049.0009.

    Google Scholar 

  18. A. M. Kurdyukov, Russ. J. Appl. Chem., 2007, 80, 1566; DOI: https://doi.org/10.1134/S1070427207090236.

    Article  CAS  Google Scholar 

  19. C.-H. Lee, S.-M. Lee, B.-H. Min, D.-S. Kim, C.-H. Jun, Org. Lett., 2018, 20, 2468; DOI: https://doi.org/10.1021/acs.orglett.8b00831.

    Article  CAS  PubMed  Google Scholar 

  20. K. B. Wiberg, T. M. Shryne, J. Am. Chem. Soc., 1955, 77, 2774; DOI: https://doi.org/10.1021/ja01615a031.

    Article  CAS  Google Scholar 

  21. S. Kajigaeshi, Y. Ueda, S. Fujisaki, T. Kakinami, Bull. Chem. Soc. Japan, 1989, 62, 2096; DOI: https://doi.org/10.1246/bcsj.62.2096.

    Article  CAS  Google Scholar 

  22. A. K. Mishra, H. Nagarajaiah, J. N. Moorthy, Eur. J. Org. Chem., 2015, 12, 2733; DOI: https://doi.org/10.1002/ejoc.201403463.

    Article  Google Scholar 

  23. P. M. Kathe, A. Berkefeld, I. Fleischer, Synlett, 2021, 32, 1629; DOI: https://doi.org/10.1055/s-0040-1706683.

    Article  CAS  Google Scholar 

  24. M. A. B. Mostafa, R. M. Bowley, D. T. Racys, M. C. Henry, A. Sutherland, J. Org. Chem., 2017, 82, 7529; DOI: https://doi.org/10.1021/acs.joc.7b01225.

    Article  CAS  PubMed  Google Scholar 

  25. K. Auwers, Ber. Dtsch. Chem. Ges., 1911, 44, 788; DOI: https://doi.org/10.1002/cber.191104401113.

    Article  CAS  Google Scholar 

  26. C. Molinaro, S. Shultz, A. Roy, S. Lau, T. Trinh, R. Angelaud, P. D. O’Shea, S. Abele, M. Cameron, Ed Corley, J.-A. Funel, D. Steinhuebel, M. Weisel, S. Krska, J. Org. Chem., 2011, 76, 1062; DOI: https://doi.org/10.1021/jo102070e.

    Article  CAS  PubMed  Google Scholar 

  27. G. A. Olah, L. Ohannesian, M. Arvanaghi, Synthesis, 1986, 10, 868; DOI: https://doi.org/10.1055/s-1986-31813.

    Article  Google Scholar 

  28. G. A. Molander, L. N. Cavalcanti, J. Org. Chem., 2011, 76, 7195; DOI: https://doi.org/10.1021/jo201313a.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. J. M. Poirier, C. Vottero, Tetrahedron, 1989, 45, 1415; DOI: https://doi.org/10.1016/0040-4020(89)80139-5.

    Article  CAS  Google Scholar 

  30. L. Y. Chen, T. Liu, X. Zhou, Z. Sun, ARKIVOC, 2014, 5, 64; DOI: https://doi.org/10.3998/ark.5550190.p008.587.

    Article  Google Scholar 

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Acknowledgments

The authors are grateful to the Collective Usage Center “Agidel” of the Ufa Federal Research Center of the Russian Academy of Sciences for the spectral research.

Funding

The study was financially supported by the Ministry of Science and Higher Education of the Russian Federation (Government contract No. FMRS-2022-0076).

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 41 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    A. R. Bayguzina, L. I. Gallyamova, R. R. Asadullin & I. R. Ramazanov

Authors
  1. A. R. Bayguzina
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  2. L. I. Gallyamova
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  3. R. R. Asadullin
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  4. I. R. Ramazanov
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Corresponding author

Correspondence to I. R. Ramazanov.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2345–2349, October, 2023.

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Bayguzina, A.R., Gallyamova, L.I., Asadullin, R.R. et al. FeBr2-catalyzed chlorination of aromatic compounds with ButOCl. Russ Chem Bull 72, 2345–2349 (2023). https://doi.org/10.1007/s11172-023-4031-7

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  • DOI: https://doi.org/10.1007/s11172-023-4031-7

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