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A Two‐Step Sequence to Ethyl α‐Fluorocyclopropanecarboxylates Through MIRC Reaction of Ethyl Dichloroacetate and Highly Regioselective Fluorination
Author(s) -
Zhang Min,
Gong Yuefa,
Wang Weizhou
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300978
Subject(s) - chemistry , regioselectivity , nucleophile , reagent , halogen , sequence (biology) , medicinal chemistry , ring (chemistry) , potassium , organic chemistry , combinatorial chemistry , catalysis , biochemistry , alkyl
A two‐step sequence to ethyl α‐fluorocyclopropanecarboxylates has been developed. Ethyl α‐chlorocyclopropanecarboxylates were first obtained through a Michael‐initiated ring closure reaction of terminal electron‐deficient olefins with ethyl 2,2‐dichloroacetate under mild basic conditions. Subsequent smooth conversion into the corresponding monofluorinated analogues in good yields was through a halogen exchange reaction with potassium bifluoride. Further investigation clearly demonstrated that potassium bifluoride in this reaction system played a dual role of base and nucleophilic reagent. This is the first successful example reported hitherto for producing ethyl α‐fluorocyclopropanecarboxylate directly through fluorination of its chlorinated analogue with alkali bifluoride.