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Letters in Organic Chemistry

Author(s): Jitander K. Kapoor, Loveena Arora* and Om Prakash

DOI: 10.2174/1570178616666190118152325

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Selective α,α-Dibromination of Arylethanones with Copper(II) Bromide

Page: [700 - 704] Pages: 5

  • * (Excluding Mailing and Handling)

Abstract

Various arylethanones including electron-rich aromatic ketones such as o-hydroxyacetophenone and its p-isomer underwent selective side-chain α,α-dibromination using a heterogeneous system consisting of four molar equivalents of copper(II) bromide in chloroform-ethyl acetate under reflux. This study provides the cleanest method for the selective synthesis of several synthetically useful α,α-dibromoketones which are otherwise difficult to prepare.

Keywords: o/p-Hydroxyacetophenone, heterogeneous system, side-chain dibromination, arylethanones, copper(II) bromide, bromoketone.

Graphical Abstract

[1]
Larock, R.C. Comprehensive Organic Transformations, 2nd ed; VCH Publishers Inc: New York, U.S.A, 1999, p. 717.
[2]
De Kimpe, N.; Verhe, R. In The Chemistry of a-Haloketones, a-Haloaldehydes and a-Haloimines; Patai, S.; and Rappport, Z., Eds.; John Wiley and Sons: Chichester, 1988, pp. 1-119.
[3]
Ngoy, B.P.; Sebej, P.; Solomek, T.; Lim, B.H.; Pastrierik, T.; Park, B.S.; Givens, R.C.; Heger, D.; Klan, P. Photochem. Photobiol. Sci., 2012, 11, 1465-1475.
[4]
Meng, L.G.; Ge, N.L.; Yang, M.M.; Wang, L. Eur. J. Org. Chem., 2011, 19, 3403-3406.
[5]
Boeykens, M.; De Kimpe, N. Tetrahedron, 1994, 50, 12349-12360.
[6]
Erian, A.W.; Sherif, S.M.; Gaber, H.M. Molecules, 2003, 8, 793-865.
[7]
Prakash, R.; Kumar, A.; Aggarwal, R.; Prakash, O.; Singh, S.P. Synth. Commun., 2007, 37, 2501-2505.
[8]
Kim, K.; Chao, J.; Yoon, S.C. J. Chem. Soc., Perkin Trans., 1995, I, 253-254.
[9]
Kim, K.; Cho, J. Heterocycles, 1994, 38, 1859-1866.
[10]
Araki, S.; Hirashita, T.; Shimizu, H.; Yamamura, H.; Kawai, M.; Butsugan, Y. Tetrahedron, 1996, 52, 2803-2816.
[11]
Kawabata, N.; Fujii, T.; Naka, M.; Yamashita, S. Bull. Chem. Soc. Jpn., 1977, 50, 1005-1015.
[12]
Furukawa, J.; Matsmura, A.; Matsuoka, Y.; Kiji, J. Bull. Chem. Soc. Jpn., 1976, 49, 829-831.
[13]
Kowalski, C.J.; Reddy, R.E. J. Org. Chem., 1992, 57, 7194-7208.
[14]
Shchepin, V.V.; Gladkova, G.E.; Russkikh, N.; Yu, J. J. Org. Chem. USSR (Engl. Transl.),, 1992, 28, 902.
[15]
Kowalski, C.J.; Fields, K.W. J. Am. Chem. Soc., 1982, 104, 321-323.
[16]
Zhdankin, V.V.; Stang, P.J. Tetrahedron Lett., 1993, 34, 1461-1462.
[17]
Coats, S.J.; Wasserman, H.H. Tetrahedron Lett., 1995, 36, 7735-7738.
[18]
Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett., 1984, 25, 2817-2820.
[19]
Stotter, P.L.; Hill, K.A. Tetrahedron Lett., 1972, 13, 4067-4070.
[20]
Prakash, R. Synthetic studies involving carbonyl compounds., Ph.D. Thesis, Kurukshetra University, Kurukshetra, India. 2007.
[21]
Prakash, R.; Kumar, A.; Aggarwal, R.; Prakash, O.; Singh, S.P. Synth. Commun., 2007, 137, 2501-2505.
[22]
Arora, L.; Sharma, N.; Kapoor, J.K. Indian J. Heterocycl. Chem., 2016, 25, 291-296.
[23]
King, L.C.; Ostrum, G.K. J. Org. Chem., 1964, 29, 3459-3461.
[24]
Jakhar, K.; Makrandi, K.J. Green Chem. Lett. Rev., 2008, 1, 219-221.
[25]
Juneja, K.S.; Choudhary, D.; Paul, S.; Gupta, R. Synth. Commun., 2006, 36, 2877-2881.
[26]
Tatar, J.; Stojanovic, M.B.; Stojanovic, M.; Markovic, R. Tetrahedron Lett., 2009, 50, 700-703.
[27]
Rosenmund, K.W.; Pfroepffer, K. Chem. Ber., 1957, 90, 1922-1928.
[28]
Buu-Hoi, N.P.; Lavitt, D. J. Chem. Soc., 1955, 910-915.
[29]
Buu-Hoi, N.P.; Xuong, N.D.; Lavitt, D. J. Chem. Soc., 1954, 1034-1038.
[30]
Terent’ev, A.O.; Khodykin, S.V.; Krylov, I.B.; Ogibin, Y.N.; Nikishin, G.I. Synthesis, 2006, 7, 1087-1092.
[31]
Lin, S.A.; Ho, C.M. Huaxue, 1983, 41, 107-111.