Skip to main content
SpringerLink
Log in

Ionic liquids bis(2-N-methylimidazoliumethyl)ether dichloroiodate/dibromochlorate as an efficient halogenating reagent for the synthesis of α-haloketones

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Bis(2-N-methylimidazoliumethyl)ether dichloroiodate/dibromochlorate is found to be an effective reagent system for the α-chlorination/bromination of carbonyl compounds. These novel solid halogenating reagents are readily prepared from an ionic liquid and molecular halogen in high yields. α-halogenation reaction occurs under mild conditions yielding the products in good to excellent yields.

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

Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. H. Veisi, R. Ghorbani-vaghei, Tetrahedron 66, 7445 (2010)

    Article  CAS  Google Scholar 

  2. H. Veisi, Curr. Org. Chem. 15, 2438 (2011)

    Article  CAS  Google Scholar 

  3. Y. Mei, P.A. Bentley, J. Du, Tetrahedron Lett. 49, 3802 (2008)

    Article  CAS  Google Scholar 

  4. T. Schlama, K. Gabriel, V. Gouverneur, C. Mioskowski, Angew. Chem. Int. Ed. Engl. 36, 2342 (1997)

    Article  CAS  Google Scholar 

  5. R.N. Ram, T.P. Manoj, J. Org. Chem. 73, 5633 (2008)

    Article  CAS  Google Scholar 

  6. M. Tajbakhsh, S. Habibzadeh, Lett. Org. Chem. 4, 512 (2007)

    Article  CAS  Google Scholar 

  7. A.S. El-Ahl, A.H. Elbeheery, F.A. Amer, Synth. Commun. 41, 1508 (2011)

    Article  CAS  Google Scholar 

  8. A. Bongini, G. Cainelli, M. Contento, F. Manescalchi, J. Chem. Soc. Chem. Commun. 1278 (1980)

  9. K.M. Brummond, K.D. Gesenberg, Tetrahedron Lett. 40, 2231 (1999)

    Article  CAS  Google Scholar 

  10. S. Kajigaeshi, T. Kakinami, M. Moriwaki, S. Fujisaki, K. Maeno, T. Okamoto, Synthesis 122, 545 (1988)

    Article  Google Scholar 

  11. G.F. Hambly, T.H. Chan, Tetrahedron Lett. 27, 2563 (1986)

    Article  CAS  Google Scholar 

  12. E.M. Kosower, W.J. Cole, G.S. Wu, D.E. Cardy, G. Meisters, J. Org. Chem. 28, 630 (1963)

    Article  CAS  Google Scholar 

  13. J.C. Lee, J.Y. Park, S.Y. Yoon, Y.H. Bae, S.J. Lee, Tetrahedron Lett. 45, 191 (2004)

    Article  CAS  Google Scholar 

  14. A.O.Terent’ev, S.V. Khodykin, N.A. Troitskii, Y.N. Ogibin, G.I. Nikishin, Synthesis 2845 (2004)

  15. P. Dowd, C. Kaufman, P. Kaufman, J. Org. Chem. 50, 882 (1985)

    Article  CAS  Google Scholar 

  16. S.J. Coats, H.H. Wasserman, Tetrahedron Lett. 36, 7735 (1995)

    Article  CAS  Google Scholar 

  17. R.E. Boyd, C.R. Rasmussen, J.B. Press, Synth. Commun. 25, 1045 (1995)

    Article  CAS  Google Scholar 

  18. S.J. Zhang, Z.G. Le, Chin. Chem. Lett. 16, 201 (2005)

    Google Scholar 

  19. Y. Izumisawa, H. Togo, GSC 1, 54 (2011)

    Article  CAS  Google Scholar 

  20. A.R. Jagdale, P.V. Chouthaiwale, A. Sudalai, Indian J. Chem. 48, 1424 (2009)

    Google Scholar 

  21. Z.G. Le, Z.C. Chen, Y. Hu, Q.G. Zheng, Synthesis 17, 2809 (2004)

    Google Scholar 

  22. C. Yue, A. Mao, Y. Wei, M. Lü, Catal. Commun. 9, 1571 (2008)

    Article  CAS  Google Scholar 

  23. L. Wang, H. Li, P. Li, Tetrahedron 65, 364 (2009)

    Article  CAS  Google Scholar 

  24. J. Yu, C. Zhang, Synthesis 2324 (2009)

  25. A.S. Burungule, S.P. Bondge, S.B. Munde, Synth. Commun. 33, 1923 (2003)

    Article  CAS  Google Scholar 

  26. S. Kajigaeshi, T. Kakinami, T. Okamoto, S. Fujisaki, Bull. Chem. Soc. Jpn. 60, 1159 (1987)

    Article  CAS  Google Scholar 

  27. I. Pravst, M. Zupan, S. Stavber, Tetrahedron 64, 5191 (2008)

    Article  CAS  Google Scholar 

  28. A.K. Macharla, R.C. Nappunni, M.R. Marri, S. Peraka, N. Nama, Tetrahedron Lett. 53, 191 (2012)

    Article  CAS  Google Scholar 

  29. G.K.S. Prakash, R. Ismail, J. Garcia, C. Panja, G. Rasul, T. Mathew, G.A. Olah, Tetrahedron Lett. 52, 1217 (2011)

    Article  CAS  Google Scholar 

  30. J.C. Lee, H.J. Park, Synth. Commun. 36, 777 (2006)

    Article  CAS  Google Scholar 

  31. H.M. Meshram, P.N. Reddy, P. Vishnu, K. Sadashiv, J.S. Yadav, Tetrahedron Lett. 47, 991 (2006)

    Article  CAS  Google Scholar 

  32. E.R. Blowt, V.W. Eagerm, D.C. Silverman, J. Am. Chem. Soc. 68, 566 (1946)

    Article  Google Scholar 

Download references

Acknowledgment

We are grateful to the Department of Chemistry, Ferdowsi University of Mashhad, for financial support (Grant No.3/15592).

Author information

Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, P.O. Box 91775-1436, Mashhad, Iran

    Hossein Eshghi, Mehdi Bakavoli, Marjan Ghasemzadeh & Seyed Mohammad Seyedi

Authors
  1. Hossein Eshghi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mehdi Bakavoli
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marjan Ghasemzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Seyed Mohammad Seyedi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hossein Eshghi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Eshghi, H., Bakavoli, M., Ghasemzadeh, M. et al. Ionic liquids bis(2-N-methylimidazoliumethyl)ether dichloroiodate/dibromochlorate as an efficient halogenating reagent for the synthesis of α-haloketones. Res Chem Intermed 41, 1673–1682 (2015). https://doi.org/10.1007/s11164-013-1302-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1302-1

Keywords

Search

Navigation