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Paper | Regular issue | Vol 68, No. 9, 2006, pp.1893-1899
Published online, 11th July, 2006
DOI: 10.3987/COM-06-10796
Bromination of Dimethyl 1-Substituted Indole-2,3-dicarboxylates

Yasuyoshi Miki,* Misako Umemoto, Mai Nakamura, Hajime Hibino, Noriko Ohkita, Akiko Kato, and Yoshiyuki Aoki

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


Treatment of dimethyl indole-2,3-dicarboxylate with pyridinium hydrobromide perbromide or bromine in the presence of Lewis acid gave dimethyl 5 bromoindole-2,3-dicarboxylate as the sole product. In a similar manner, dimethyl 1-benzyl- and 1-benzenesulfonyl-indole-2,3-dicarboxylates provided a mixture of the corresponding 5 bromoindole and 6-bromoindole derivatives. However, methyl 1-trifluoromethanesulfonylindole-2,3-dicarboxylate gave methyl 6-bromo-1-trifluoromethanesulfonylindole-2,3-dicarboxylate as a major product.