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http://dx.doi.org/10.5012/jkcs.2011.55.2.240

Highly Convenient and Large Scale Synthesis of 5-chloroindole and its 3-substituted Analogues  

Keetha, Laxminarayana (Institute of Science and Technology, Jawaharlal Nehru Technological University)
Palle, Sadanandam (Institute of Science and Technology, Jawaharlal Nehru Technological University)
Ramanatham, Vinodkumar (Institute of Science and Technology, Jawaharlal Nehru Technological University)
Khagga, Mukkanti (R&D Center, Suven Life Sciences Ltd.)
Chinnapillai, Rajendiran (R&D Center, Suven Life Sciences Ltd.)
Publication Information
Journal of the Korean Chemical Society / v.55, no.2, 2011 , pp. 240-242 More about this Journal
Abstract
A large scale and commercially feasible synthesis of 5-chloroindole and its 3-substituted analogues has been described via a halogen - halogen exchange reaction from 5-bromoindole and its derivatives using cuprous chloride and dipolar aprotic solvent N-methyl-2-pyrrolidone in one pot with good yields.
Keywords
5-haloindoles; copper (I) chloride; N-methyl-2-pyrrolidone; halogen-halogen exchange;
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Times Cited By KSCI : 1  (Citation Analysis)
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1 Gall, W. G.; Astill, B. D.; Boekelheide, V. J. Org. Chem. 1958, 20, 1538.
2 Ikan, R.; Hoffmann, E.; Bergmann, E. D.; Galum, A. Israel J. Chem. 1964, 1, 37.
3 Kasahara, A.; Izumi, T.; Kikuchi, T.; Xiao-Ping, L. J. Het. Chem. 1987, 24, 1555.   DOI
4 Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K. J. Org. Chem. 1988, 53, 1170.   DOI
5 Maurer, M.; Orth, W.; Fickert, W. Fr. Demande 1982, 22 pp. FR 2490638 A1 19820326 CAN 97:92135 AN 1982, 492135.
6 Moriarty, R. M.; Ku, Y. Y.; Gill, U. S. Organometallics, 1988, 7, 660.   DOI
7 Cho, C. S.; Lee, M. J.; Shim, S. C.; Kim, M. C. Bull. Korean Chem. Soc. 1999, 20, 119.
8 Cho, C. S.; Kim, J. H.; Kim, T.-J.; Shim, S. C. Tetrahedron 2001, 57, 3321.   DOI
9 Nomura, Y.; Kawashita, Y.; Hayashi, M. Heterocycles 2007, 74, 629.   DOI
10 Cho, C. S.; Park, D. C.; Shim, S. C. Bull. Korean Chem. Soc. 2007, 28, 832.   DOI
11 Hajime, A.; Hitomi, S. Bull. Chem. Soc. Jpn. 1999, 72, 787.   DOI
12 Schlosser, M, Cottet, F. Euro. J. Org. Chem. 2002, 24, 4181.
13 Russel, H. F.; Harris, B. J.; Hood, D. B.; Thompson, E. G.; Watkins, A. D.; Williams, R. D. Organic Preparations and Procedures INT. 1985, 17, 391-399.   DOI
14 Craig, P. N. Comprensive Medicinal Chemistry, Vol. 8; Drayton, C. J, Ed; Pergamon: New York, 1991
15 Southon, I. W.; Buckingham, J. In Dictionary of Alkaloids; Saxton, J.E., Ed. Champman & Hall: London, 1989.
16 Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
17 Young, E. H. P. J. Chem. Soc. 1958, 3493.   DOI
18 Baudin, J.-B.; Commenil, M.-G.; Julia, S. A.; Lorne, R.; Mauclaire, L. Bulletin de la Societe Chimique de France 1996, 133, 329.
19 Tsutomu, S, Makoto, A.; Kazuyuki, S.; Akiko, K. J. Org. Chem. 1979, 44, 578.   DOI