Article Sidebar

Download
PDF

Main Article Content

Abstract

A facile, efficient, environmentally benign protocol has been developed for rapid synthesis of α-bromoacetophenones from direct reaction of acetophenones and N-bromosuccinimide by using ultrasound waves within 15-20 min with good to excellent yields. Their formation characterized by IR, 1H NMR and mass spectroscopy.

Keywords

Ultrasound Selective monobromination a-Bromo acetophenones PEG-400; N-Bromosuccinimide

Article Details

How to Cite
S. Wagare, D., Farooqui, M., D. Vilaytkar, N., & N. Durrani, A. (2017). An Efficient and Selective α-Monobromination of Aromatic Ketones under Ultrasonic Irradiation in Aqueous Medium. Asian Journal of Organic & Medicinal Chemistry, 2(4), 165–168. https://doi.org/10.14233/ajomc.2017.AJOMC-P86
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. A.W. Erian, S.M. Sherif and H.M. Gaber, Molecules, 8, 793 (2003); https://doi.org/10.3390/81100793.
  2. G. Sabitha and A.V.S. Rao, Synth. Commun., 17, 341 (1987); https://doi.org/10.1080/00397918708077315.
  3. N. Jain, N. Devi and H.G. Krishnamurthy, Indian J. Chem., 33B, 1085 (1994).
  4. K.V.V. Reddy, P.S. Rao and D. Ashok, Synth. Commun., 30, 1825 (2000); https://doi.org/10.1080/00397910008087228.
  5. L.G. Minyaeva, O.M. Golyanskaya and V.V. Mezheritskii, Org. Khim., 30, 258 (1994); Chem. Abstr., 122, 160425 (1995).
  6. D.S. Wagare, D. Lingampalle, M. Farooqui and A. Durrani, Der Pharma Chemica, 8, 408 (2016).
  7. D.S. Wagare, M. Farooqui, T.D. Keche and A. Durrani, Synth. Commun., 46, 1741 (2016); https://doi.org/10.1080/00397911.2016.1223314.
  8. Y.J. Miyahara, Heterocycl. Chem., 16, 1147 (1979); https://doi.org/10.1002/jhet.5570160612.
  9. F.G. Medina, J.G. Marrero, M. Macías-Alonso, M.C. González, I. Córdova-Guerrero, A.G. Teissier García and S. Osegueda-Robles, Nat. Prod. Rep., 32, 1472 (2015); https://doi.org/10.1039/C4NP00162A.
  10. R.B.N. Baig and R.S. Varma, Chem. Soc. Rev., 41, 1559 (2012); https://doi.org/10.1039/C1CS15204A.
  11. H. Zang, Y. Zhang, Y. Zang and B.W. Cheng, Ultrason. Sonochem., 17, 495 (2010); https://doi.org/10.1016/j.ultsonch.2009.11.003.
  12. M.R.P. Heravi, Ultrason. Sonochem., 16, 361 (2009); https://doi.org/10.1016/j.ultsonch.2008.11.001.
  13. K.K. Rajbongshi, D. Hazarika and P. Phukan, Tetrahedron Lett., 56, 356 (2015); https://doi.org/10.1016/j.tetlet.2014.11.096.
  14. K. Gewald, H.J. Jaensch and O. Calderon, East German Patent, 113359 (1975); Chem. Abstr., 84, 135647 (1976).
  15. M. Kidwai, B. Dave and K.R. Bhushan, Chem. Pap., 54, 231 (2000).
  16. D.E. Tupper, T.M. Hotten and W.G. Prowse, J. Heterocycl. Chem., 33, 1123 (1996); https://doi.org/10.1002/jhet.5570330420.
  17. P. Molina, A. Ferao, P.M. Fresneda, A. Lorenzo and A. Tarraga, J. Heterocycl. Chem., 20, 381 (1983); https://doi.org/10.1002/jhet.5570200222.
  18. V.V. Kuz’menko, T.A. Kuz’menko, A.F. Pozharskii and O.V. Kryshtalyuk, Khim. Geterotsikl. Soedin., 1689 (1990); Chem. Abstr., 114, 207130 (1991).
  19. P. Molina, A. Arques, M. de los Desamparados Velasco and J.M. Villalgordo, Heterocycles, 26, 1323 (1987); https://doi.org/10.3987/R-1987-05-1323.
  20. I.M.A. Awad, A.E. Abdel-Rahman and E.A. Bakite, J. Chem. Technol. Biotechnol., 51, 483 (1991); https://doi.org/10.1002/jctb.280510406.
  21. K. Prasad, D.V. Pinjari, A.B. Pandit and S.T. Mhaske, Ultrason. Sonochem., 17, 409 (2010); https://doi.org/10.1016/j.ultsonch.2009.09.003.
  22. R.M. Srivastava, R.A.W. Neves Filho, C.A. da Silva and A.J. Bortoluzzi, Ultrason. Sonochem., 16, 737 (2009); https://doi.org/10.1016/j.ultsonch.2009.04.006.
  23. A. Duarte, W. Cunico, C.M.P. Pereira, A.F.C. Flores, R.A. Freitag and G.M. Siqueira, Ultrason. Sonochem., 17, 281 (2010); https://doi.org/10.1016/j.ultsonch.2009.08.004.
  24. K.J. Jarag, D.V. Pinjari, A.B. Pandit and G.S. Shankarling, Ultrason. Sonochem., 18, 617 (2011); https://doi.org/10.1016/j.ultsonch.2010.09.010.
  25. C. Petrier and J.-L. Luche, ed.: J.-L. Luche, Synthetic Organic Sono-chemistry, Plenum Press, New York, Chap. 2, pp. 53-56 (1998).
  26. B. Toukoniitty, E. Toukoniitty, P. Mäki-Arvela, J.-P. Mikkola, T. Salmi, D.Y. Murzin and P.J. Kooyman, Ultrason. Sonochem., 13, 68 (2006); https://doi.org/10.1016/j.ultsonch.2004.11.001.
  27. A. Santagati, M. Santagati and M. Modica, Heterocycles, 36, 1315 (1993); https://doi.org/10.3987/COM-92-6304.
  28. K. Makino, M.M. Mossoba and P. Riesz, J. Am. Chem. Soc., 104, 3537 (1982); https://doi.org/10.1021/ja00376a064.
  29. J.H. Bang and K.S. Suslick, Adv. Mater., 22, 1039 (2010); https://doi.org/10.1002/adma.200904093.
  30. D. S. Wagare, D. Lingampalle, M. Farooqui and A. Durrani, Der Pharma Chemica, 8, 408 (2016).
  31. X.-Y. Guan, Z. Al-Misba'aa and K.-W. Huang, Arabian J. Chem., 8, 892 (2014); https://doi.org/10.1016/j.arabjc.2014.01.024.
  32. P. Bhosale, R.S. Chavan and P.V. Bhosale, Indian J. Chem., 51B, 1649 (2012).