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Note | Regular issue | Vol 78, No. 11, 2009, pp.2845-2850
Published online, 7th September, 2009
DOI: 10.3987/COM-09-11802
Decarboxylative Bromination of Indole-2,3-dicarboxylic Acids Using Oxone® or CAN in the Presence of Lithium Bromide

Hideaki Umemoto, Misako Umemoto, Chiaki Ohta, Masashi Dohshita, Hiroki Tanaka, Syo Hattori, Hiromi Hamamoto, and Yasuyoshi Miki*

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

The treatment of 1-methylindole-2,3-dicarboxylic acid with Oxone® and lithium bromide produced 3,3-dibromo-1-methyloxindole. However, the reaction of 1-benzenesulfonylindole-2,3-dicarboxylic acid with Oxone® and lithium bromide afforded 1-benzenesulfonyl-2,3-dibromoindole. In a similar manner, 2,3,5,6-tetrabromoindole was synthesized from 1-benzenesulfonyl-5,6-dibromoindole-2,3-dicarboxylic acid.