Synthesis 2015; 47(20): 3241-3245
DOI: 10.1055/s-0034-1378747
paper
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of 2-Fluoro- and 2-Chloromalonic Esters Mediated by Hypervalent Iodine

Tsugio Kitamura*
Department of Chemistry of Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
,
Kensuke Muta
Department of Chemistry of Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
,
Juzo Oyamada
Department of Chemistry of Applied Chemistry, Graduate School of Science and Engineering, Saga University, Hojo-machi, Saga 840-8502, Japan   Email: kitamura@cc.saga-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 26 May 2015

Accepted after revision: 29 June 2015

Publication Date:
12 August 2015 (online)


Abstract

Direct fluorination of malonic esters with a reagent system of iodosylbenzene and Et3N·5HF gave the corresponding 2-fluoromalonic esters in good to high yields. Direct chlorination using iodosylbenzene and hydrochloric acid also provided the 2-chloromalonates in high yields.

Supporting Information