Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone

Gambacorta, Guido; Baxendale, Ian R.

doi:10.1021/acs.oprd.1c00440

Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone

Gambacorta, Guido; Baxendale, Ian R.

Authors

Guido Gambacorta

Professor Ian Baxendale i.r.baxendale@durham.ac.uk
Professor

Abstract

A continuous-flow preparation of 2-benzoxazolinone via the Hofmann rearrangement of salicylamide has been implemented employing trichloroisocyanuric acid as the stable and atom-economic chlorinating agent. The system was optimized to avoid solid accumulation and allow the preparation of hundreds of grams of the pure desired material over a working day. Furthermore, a trichloroisocyanuric acid (TCCA)-based chlorination of 2-benzoxazolone to the corresponding 5-chloro derivative was also carried out under batch conditions.

Citation

Gambacorta, G., & Baxendale, I. R. (2022). Continuous-Flow Hofmann Rearrangement Using Trichloroisocyanuric Acid for the Preparation of 2-Benzoxazolinone. Organic Process Research and Development, 26, 422-430. https://doi.org/10.1021/acs.oprd.1c00440

Journal Article Type	Article
Online Publication Date	Feb 18, 2022
Publication Date	2022
Deposit Date	Aug 24, 2022
Publicly Available Date	Aug 24, 2022
Journal	Organic Process Research & Development
Print ISSN	1083-6160
Electronic ISSN	1520-586X
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	26
Pages	422-430
DOI	https://doi.org/10.1021/acs.oprd.1c00440

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2022 American Chemical Society.
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