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

Gambacorta, Guido; Baxendale, Ian R.

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
• Public URL: https://durham-repository.worktribe.com/output/1193687