Synthesis 2003(15): 2410-2414  
DOI: 10.1055/s-2003-42412
PAPER
© Georg Thieme Verlag Stuttgart · New York

The First Direct Chlorination of Iodoarenes - A Side-chain Directed Process

Daniela Mirka, Olga Kataevab, Roland Fröhlicha, Siegfried R. Waldvogel*a
a Westfälische Wilhelms-Universität Münster, Org.-Chem. Institut, Corrensstr. 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: waldvog@uni-muenster.de;
b H. E. Arbuzov Institute, Arbuzov Street 8, Kazan 420088, Russia
Further Information

Publication History

Received 22 July 2003
Publication Date:
29 September 2003 (online)

Abstract

The chlorination of electron rich iodoarenes with MoCl5 proceeds with methoxycarbonylmethyl as the directing group. The transformation is selective and without loss of the valuable iodo substituent.

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All isomeric products could not be separated on a preparative scale. NMR spectra of the mixture clearly identified the chlorinated compounds and further characterization was successfully performed by GC-MS methods.

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Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC 211377. Copies of the data can be obtained free of charge on application to The Director CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336-033, e-mail: deposit@ccdc.cam.ac.uk].