Synthesis 2012; 44(8): 1159-1162
DOI: 10.1055/s-0031-1290578
special topic
© Georg Thieme Verlag Stuttgart · New York

Convenient Chlorination with Concentrated Hydrochloric Acid in the Presence of Iodosylbenzene

Tsugio Kitamura*
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan, Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Yui Tazawa
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan, Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Mohammad Hasan Morshed
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan, Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
,
Soichi Kobayashi
Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan, Fax: +81(952)288548   Email: kitamura@cc.saga-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 17 February 2012

Accepted: 20 February 2012

Publication Date:
22 March 2012 (online)

Abstract

An efficient chlorination of β-keto esters, 1,3-diketones, and alkenes was performed conveniently with concentrated HCl in the presence of PhIO, selectively giving α-chloro-β-keto esters, 2-chloro-1,3-diketones, and 1,2-dichloroalkanes, respectively. It was suggested that the chlorination took place with (dichloroiodo)benzene generated in situ. A selective anti-addition was observed in the chlorination of indene.

 
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