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Communication | Regular issue | Vol 22, No. 2, 1984, pp.241-244
Published online, 1st January, 1970
DOI: 10.3987/R-1984-02-0241
The Friedel-Crafts Acylation of Ethyl Indole-2-carboxylate. An Unusual Substitution on the Benzene Moiety

Yasuoki Murakami,* Masanobu Tani, Kenjiro Tanaka, and Yuusaku Yokoyama

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Ethyl indole-2-carboxylate can be acylated with a variety of acyl chlorides under Friedel-Crafts conditions to give mono-acyl indole derivatives. However, the acyl chloride derived from a stronger acid tends to substitute at the C-5 position rather than at the C-3, a usual nucleophilic center of indoles.