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A Convergent Continuous Multistep Process for the Preparation of C4-Oxime-Substituted Thiazoles

Published version
Peer-reviewed

Type

Article

Change log

Authors

Godineau, E 
Battilocchio, C 
Lehmann, M 
Ley, SV 

Abstract

We report a strategy designed for the rapid and convergent assembly of C4-oxime substituted thiazoles. Our approach relied on 3-bromo-2-oxopropanal O-methyl oxime 7 as a key building block. A three-step sequence to 7 was designed, which for safety concerns, could only be operated in batch mode on limited scales (<< 100g). We describe herein how we addressed such a limitation, by designing a multistep continuous synthesis of this intermediate and further demonstrate the advantages of flow reactor configuration upon scaling up.

Description

Keywords

Bromination, continuous processing, hazardous chemistry, thiazole synthesis

Journal Title

Organic Process Research and Development

Conference Name

Journal ISSN

1083-6160
1520-586X

Volume Title

22

Publisher

American Chemical Society
Sponsorship
Engineering and Physical Sciences Research Council (EP/K009494/1)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Engineering and Physical Sciences Research Council (EP/M004120/1)
Syngenta