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

Direct fluorination of malonic esters with a reagent system of iodosylbenzene and Et3N center dot 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.

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 20; pp. 3241 - 3245
Main Authors Kitamura, Tsugio, Muta, Kensuke, Oyamada, Juzo
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.10.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
XENON DIFLUORIDE
2-chloromalonic esters
hydrogen fluoride
BETA-DICARBONYL COMPOUNDS
EFFICIENT METHOD
FACILE SYNTHESIS
iodosylbenzene
ELEMENTAL FLUORINE
IODOTOLUENE DIFLUORIDE
hydrochloric acid
ALPHA-FLUORINATION
DERIVATIVES
2-fluoromalonic esters
HF
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Summary:Direct fluorination of malonic esters with a reagent system of iodosylbenzene and Et3N center dot 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.
Bibliography:KAKEN
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1378747