Development of a Safe and Robust Process for the Large-Scale Preparation of a Vinyl Bromide from a Ketone Using a (PhO)3P/Br2‑Derived Reagent

The large-scale synthesis of ethyl 4-bromocyclohex-3-enecarboxyalate, using a mild brominating reagent derived from triphenyl phosphite and bromine, is reported. The development and comparison of both continuous and batch processes are described. A modified addition sequence was developed based on t...

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Bibliographic Details
Published in:Organic process research & development 2016-05, Vol.20 (5), p.977-981
Main Authors: Likhite, Nachiket, Ramasamy, Sivaraj, Tendulkar, Shankar, Sathasivam, Shunmugaraj, Luzung, Michael, Zhu, Ye, Strotman, Neil, Nye, Jeffrey, Ortiz, Adrian, Kiau, Susanne, Eastgate, Martin D, Vaidyanathan, Rajappa
Format: Article
Language:English
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Summary:The large-scale synthesis of ethyl 4-bromocyclohex-3-enecarboxyalate, using a mild brominating reagent derived from triphenyl phosphite and bromine, is reported. The development and comparison of both continuous and batch processes are described. A modified addition sequence was developed based on the knowledge garnered from flow-processing, resulting in a safe and efficient process for the in situ generation of the unstable active reagent and its immediate reaction with the ketone in a batch mode process.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.6b00100