Efficient and scalable synthesis of ethyl 2,6-dichloro-5-fluoronicotinoyl acetate using the Blaise reaction as a key step

An efficient synthesis of 2,6-dichloro-5-fluoronicotinoyl acetate (1) has been accomplished in a single step using the Blaise reaction of ethyl bromoacetate with 3-cyano-2,6-dichloro-5-fluoropyridine (4). Use of methanesulfonic acid as an in situ activator of zinc removed the induction period of the...

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Published inOrganic process research & development Vol. 9; no. 3; pp. 311 - 313
Main Authors Choi, BS, Chang, JH, Choi, HW, Kim, YK, Lee, KK, Lee, KW, Lee, JH, Heo, T, Nam, DH, Shin, H
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.05.2005
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
(1-ALPHA,5-ALPHA,6-ALPHA)-6-AMINO-3-AZABICYCLO<3.1.0>HEXANE
ROUTE
ACID
ESTERS
INTERMEDIATE
ALPHA
ANTIBACTERIAL AGENTS
DERIVATIVES
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Summary:An efficient synthesis of 2,6-dichloro-5-fluoronicotinoyl acetate (1) has been accomplished in a single step using the Blaise reaction of ethyl bromoacetate with 3-cyano-2,6-dichloro-5-fluoropyridine (4). Use of methanesulfonic acid as an in situ activator of zinc removed the induction period of the Blaise reaction to render it safe and viable for a large-scale operation.
ISSN:1083-6160
1520-586X
DOI:10.1021/op050012a