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Research on Chemical Intermediates

, Volume 39, Issue 9, pp 4121–4125 | Cite as

One-pot synthesis of 6-bromo-4,4-dimethylthiochroman

  • Shaodong Zhou
  • Zutai Liao
  • Jixin Yuan
  • Chao Qian
  • Xinzhi Chen
Article
  • 357 Downloads

Abstract

One-pot synthesis of 6-bromo-4,4-dimethylthiochroman from bromobenzene is reported. The crucial connection between the three steps is that the byproducts in the first two steps are used as the catalyst in the third step. Compared with the previous route, this approach is of low consumption and low pollution.

Keywords

One-pot synthesis 6-Bromo-4,4-dimethylthiochroman Byproduct utilization Heterocyclic 1-Bromo-3-methylbut-2-ene 

Notes

Acknowledgments

The authors gratefully acknowledge funding support by grants from the National Natural Science Foundation of China (no. 21076183) and from the Science and Technology Innovation Team of Zhejiang Province (no. 2009R50002).

References

  1. 1.
    S. Frigoli, C. Fuganti, L. Malpezzi, S. Serra, Org. Process Res. Dev. 9, 646–650 (2005)CrossRefGoogle Scholar
  2. 2.
    C.N. Raut, R.B. Mane, S.M. Bagul, R.A. Janrao, P.P. Mahulikar, Arkivoc xi, 105–114 (2009)CrossRefGoogle Scholar
  3. 3.
    J.L. Duffy, J. Bao, D.L. Ondeyka, S. Tyagarajan, P. Shao, F. Ye, R. Katipally, A. Zwicker, E.C. Sherer, M.A. Plotkin, R. Moningka, Z. Hussian, H.B. Wood, F. Ujjainwalla, A. Romero, P. Finke, Y. Zang, W. Liu, WO 2012024183, 2012Google Scholar
  4. 4.
    K.Y. Tsang, S. Sinha, X. Liu, S. Bhat, R.A. Chandraratna, US 20050148590, 2005Google Scholar
  5. 5.
    M.E. Garst, L.J. Dolby, N.A. Fedoruk, US 5420295, 1995Google Scholar
  6. 6.
    J.S. Babu, C.H. Khanduri, J.B. Shah, G.J. Chavan, R.C. Aryan, Y. Kumar, WO 2006040644, 2006Google Scholar
  7. 7.
    S. Frigoli, C. Fuganti, S. Serra, F. Pizzocaro, A. Bedeschi, P. Tubertini, EP 1700855, 2006Google Scholar
  8. 8.
    S. Samanta, K. Srikanth, S. Banerjee, B. Debnath, S. Gayen, T. Jha, Bioorg. Med. Chem. 12, 1413–1423 (2004)CrossRefGoogle Scholar
  9. 9.
    M.-Q. Chen, Harbin Gongye Daxue Xuebao 34, 232–237 (2002)Google Scholar
  10. 10.
    H. Uchiro, S. Kobayashi, Tetrahedron Lett. 40, 3179–3182 (1999)CrossRefGoogle Scholar
  11. 11.
    R.F. Nystrom, W.G. Brown, J. Am. Chem. Soc. 69, 1197–1199 (1947)CrossRefGoogle Scholar
  12. 12.
    A. Nose, T. Kudo, Chem. Pharm. Bull. 35, 1770–1776 (1987)CrossRefGoogle Scholar
  13. 13.
    E.V. Bellale, M.K. Chaudhari, K.G. Akamanchi, Synthesis-Stuttgart. 3211–3213, (2009)Google Scholar
  14. 14.
    G.K.S. Prakash, T. Mathew, C. Panja, G.A. Olah, J. Org. Chem. 72, 5847–5850 (2007)CrossRefGoogle Scholar
  15. 15.
    Y.W. Jiang, Y.X. Qin, S.W. Xie, X.J. Zhang, J.H. Dong, D.W. Ma, Org. Lett. 11, 5250–5253 (2009)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  • Shaodong Zhou
    • 1
  • Zutai Liao
    • 2
  • Jixin Yuan
    • 2
  • Chao Qian
    • 1
  • Xinzhi Chen
    • 1
  1. 1.State Key Laboratory of Chemical Engineering, Department of Chemical and Biological EngineeringZhejiang UniversityHangzhouChina
  2. 2.Jiangxi Renming Pharmaceutical Chemicals Ltd.JiujiangChina

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