Ammonium persulphate promoted synthesis of polyethylene glycol entrapped potassium tribromide and its application in acylation and bromination of some selective organic compounds

Rupa Rani Dey Siddhartha Sankar Dhar

Citation:  Rupa Rani Dey, Siddhartha Sankar Dhar. Ammonium persulphate promoted synthesis of polyethylene glycol entrapped potassium tribromide and its application in acylation and bromination of some selective organic compounds[J]. Chinese Chemical Letters, 2013, 24(10): 866-868. shu

Ammonium persulphate promoted synthesis of polyethylene glycol entrapped potassium tribromide and its application in acylation and bromination of some selective organic compounds

    通讯作者: Siddhartha Sankar Dhar,
  • 基金项目:

    Technology, DST, New Delhi, India, for financial assistance received through a SERC fast track project (No. SR/FTP/CS-100/2007). (No. SR/FTP/CS-100/2007)

摘要: In this study, a new method of synthesis of polyethylene glycol supported potassium tribromide (PEG KBr3) and its application in acylation and bromination reactions are reported. Ammonium persulphate oxidizes KBr to the corresponding tribromide which is entrapped by polyethylene glycol leading to stable PEG KBr3. The reagent is proved to be highly efficient for the acylation of variety of alcohols and bromination of activated aromatic substrates. Themethod is a mild, one pot reaction and involves no use of toxic reagents.

English

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    1. [1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and practice, Oxford University Press, New York, 1998.[1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and practice, Oxford University Press, New York, 1998.

    2. [2] S. Wenda, S. Illner, A. Mell, et al., Industrial biotechnology—the future of green chemistry, Green Chem. 13 (2011) 3007-3047.[2] S. Wenda, S. Illner, A. Mell, et al., Industrial biotechnology—the future of green chemistry, Green Chem. 13 (2011) 3007-3047.

    3. [3] C. Chiappe, E. Leandri, D. Pieraccini, Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromides as reagent/solvent, J. Chem. Soc. Chem. Commun. 45 (2004) 2536-2537.[3] C. Chiappe, E. Leandri, D. Pieraccini, Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromides as reagent/solvent, J. Chem. Soc. Chem. Commun. 45 (2004) 2536-2537.

    4. [4] A.D. Jordan, C. Luo, A.B. Reitz, Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethyl ammonium tribromides, J. Org. Chem. 68 (2003) 8693-8696.[4] A.D. Jordan, C. Luo, A.B. Reitz, Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethyl ammonium tribromides, J. Org. Chem. 68 (2003) 8693-8696.

    5. [5] K. Ma, S. Li, R.G.Weiss, Stereoselective bromination reactions using tridecylmethylphosphonium tribromide in a "Stacked" reactor, Org. Lett. 10 (2008) 4155-4158.[5] K. Ma, S. Li, R.G.Weiss, Stereoselective bromination reactions using tridecylmethylphosphonium tribromide in a "Stacked" reactor, Org. Lett. 10 (2008) 4155-4158.

    6. [6] A.R. Hajipour, S.A. Pourmousavi, A.E. Ruoho, Benzyltriphenylphosphonium tribromide: a mild, regenerable and efficient reagent for the deprotection of dithioacetals, J. Sulfur Chem. 25 (2004) 401-405.[6] A.R. Hajipour, S.A. Pourmousavi, A.E. Ruoho, Benzyltriphenylphosphonium tribromide: a mild, regenerable and efficient reagent for the deprotection of dithioacetals, J. Sulfur Chem. 25 (2004) 401-405.

    7. [7] V. Kavala, S. Naik, B.K. Patel, A new recyclable ditribromide reagent for efficient bromination under solvent free condition, J. Org. Chem. 70 (2005) 4267-4271.[7] V. Kavala, S. Naik, B.K. Patel, A new recyclable ditribromide reagent for efficient bromination under solvent free condition, J. Org. Chem. 70 (2005) 4267-4271.

    8. [8] M. Dey, S.S. Dhar, M. Kalita, Novel methods of synthesis of quaternary ammonium tribromides and investigation of catalytic role of benzyltrimethyl ammonium tribromide in oxidation alcohols to carbonyl compounds, Synth. Commun. 43 (2013) 1734-1742.[8] M. Dey, S.S. Dhar, M. Kalita, Novel methods of synthesis of quaternary ammonium tribromides and investigation of catalytic role of benzyltrimethyl ammonium tribromide in oxidation alcohols to carbonyl compounds, Synth. Commun. 43 (2013) 1734-1742.

    9. [9] M. Dey, S.S. Dhar, Synthesis of quaternary tribromides: a novel green approach, Green Chem. Lett. Rev. 5 (2012) 639-642.[9] M. Dey, S.S. Dhar, Synthesis of quaternary tribromides: a novel green approach, Green Chem. Lett. Rev. 5 (2012) 639-642.

    10. [10] R. Borah, A.J. Thakur, Green synthesis of tetraalkylammonium tribromide using cerium (IV) ammonium nitrate (CAN) as oxidant, Synth. Commun. 37 (2007) 933-939.[10] R. Borah, A.J. Thakur, Green synthesis of tetraalkylammonium tribromide using cerium (IV) ammonium nitrate (CAN) as oxidant, Synth. Commun. 37 (2007) 933-939.

    11. [11] U. Bora, M.K. Chaudhuri, S.S. Dhar, et al., Peroxometal-mediated environmentally favourable route to brominating agents and protocol for the bromination of organics, Pure Appl. Chem. 73 (2001) 93-102.[11] U. Bora, M.K. Chaudhuri, S.S. Dhar, et al., Peroxometal-mediated environmentally favourable route to brominating agents and protocol for the bromination of organics, Pure Appl. Chem. 73 (2001) 93-102.

    12. [12] M. K. Chaudhuri, U. Bora, S.S. Dhar, et al., Process of preparing quaternary ammonium tribromides, US Patent 7005548 (2006).[12] M. K. Chaudhuri, U. Bora, S.S. Dhar, et al., Process of preparing quaternary ammonium tribromides, US Patent 7005548 (2006).

    13. [13] M. Dey, K. Deb, S.S. Dhar, VO(acac)2 catalysed condensation of o-phenylenediamine with aromatic carboxylic acids/aldehydes under microwave radiation affording benzimidazoles, Chin. Chem. Lett. 22 (2011) 296-299.[13] M. Dey, K. Deb, S.S. Dhar, VO(acac)2 catalysed condensation of o-phenylenediamine with aromatic carboxylic acids/aldehydes under microwave radiation affording benzimidazoles, Chin. Chem. Lett. 22 (2011) 296-299.

    14. [14] M.A. Zolfigol, G. Chehardoli, S. Salehzadeh, et al., {[K 18-Crown-6]Br3}n: a unique tribromide-type and columnar nanotube-like structure for the oxidative coupling of thiols and bromination of some aromatic compounds, Tetrahedron Lett. 48 (2007) 7969-7973.[14] M.A. Zolfigol, G. Chehardoli, S. Salehzadeh, et al., {[K 18-Crown-6]Br3}n: a unique tribromide-type and columnar nanotube-like structure for the oxidative coupling of thiols and bromination of some aromatic compounds, Tetrahedron Lett. 48 (2007) 7969-7973.

    15. [15] M. Hossein, K. Zahra, Synthesis and application of poly (diallyldimethylammonium tribromide) as a novel polymeric brominating agent, Chin. J. Chem. 28 (2010) 2221-2225.[15] M. Hossein, K. Zahra, Synthesis and application of poly (diallyldimethylammonium tribromide) as a novel polymeric brominating agent, Chin. J. Chem. 28 (2010) 2221-2225.

    16. [16] K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed., John Wiley & Sons Inc., New York, 1997p. 169.[16] K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 5th ed., John Wiley & Sons Inc., New York, 1997p. 169.

    17. [17] T. Ozeki, H. Yuasa, Y. Kanaya, Application of the solid dispersion method to the controlled release of medicine. IX. Difference in the release of flurbiprofen from solid dispersions with poly(ethylene oxide) and hydroxypropylcellulose and the interaction between medicine and polymers, Int. J. Pharm. 155 (1997) 209-217.[17] T. Ozeki, H. Yuasa, Y. Kanaya, Application of the solid dispersion method to the controlled release of medicine. IX. Difference in the release of flurbiprofen from solid dispersions with poly(ethylene oxide) and hydroxypropylcellulose and the interaction between medicine and polymers, Int. J. Pharm. 155 (1997) 209-217.

    18. [18] K. Shameli, M.B. Ahmad, S.D. Jazayeri, Synthesis and characterization of polyethylene glycol mediated silver nanoparticles by the green method, Int. J. Mol. Sci. 13 (2012) 6639-6650.[18] K. Shameli, M.B. Ahmad, S.D. Jazayeri, Synthesis and characterization of polyethylene glycol mediated silver nanoparticles by the green method, Int. J. Mol. Sci. 13 (2012) 6639-6650.

    19. [19] E. Kang, J. Robinson, K. Park, et al., Paclitaxel distribution in poly(ethylene glycol)/poly(lactide-co-glycolic acid) blends and its release visualized by coherent anti-Stokes Raman scattering microscopy, J. Control. Release 122 (2007) 261-268.[19] E. Kang, J. Robinson, K. Park, et al., Paclitaxel distribution in poly(ethylene glycol)/poly(lactide-co-glycolic acid) blends and its release visualized by coherent anti-Stokes Raman scattering microscopy, J. Control. Release 122 (2007) 261-268.

    20. [20] V. Meisalo, O. Inkinen, An X-ray diffraction analysis of potassium bromide, Acta Crystallogr. 22 (1967) 58-65.[20] V. Meisalo, O. Inkinen, An X-ray diffraction analysis of potassium bromide, Acta Crystallogr. 22 (1967) 58-65.

    21. [21] H.B. Watson, The reaction of bromine with aliphatic acids. Catalytic effect of acyl halides, J. Chem. Soc. Trans. 127 (1925) 2067-2082.[21] H.B. Watson, The reaction of bromine with aliphatic acids. Catalytic effect of acyl halides, J. Chem. Soc. Trans. 127 (1925) 2067-2082.

    22. [22] J. Buckinghum, S.M. Donaghy, Dictionary of Organic Compounds, 6th ed., Chapman & Hall, London, 1982.[22] J. Buckinghum, S.M. Donaghy, Dictionary of Organic Compounds, 6th ed., Chapman & Hall, London, 1982.

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  • 收稿日期:  2013-04-24
  • 网络出版日期:  2013-05-22
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