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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 182, 2007 - Issue 12
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Original Articles

Aromatic Chlorination with Thionyl Chloride. Applications in the Synthesis of Chlorinated Isoflavones

Otto Soidinsalo Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, Finland
&
Kristiina Wähälä Laboratory of Organic Chemistry, Department of Chemistry, University of Helsinki, Finland
Pages 2761-2767 | Received 26 Mar 2007, Accepted 12 Jun 2007, Published online: 03 Dec 2007
 
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Abstract

Genistein ( 1 ) undergoes selective chlorination on treatment with thionyl chloride to give first 8-chlorogenistein ( 10 ) and then 6,8-dichlorogenistein ( 8 ). Biochanin A ( 18 ) gives the 6,8-dichloro derivative 19 . A mechanism is suggested for the unexpected aromatic chlorinations.

Otto Soidinsalo wishes to thank Dr. Jorma Matikainen for guidance in HRMS.

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