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• W2334113710 abstract "A continuous-flow protocol for the bromination of benzylic compounds with N-bromosuccinimide (NBS) is presented. The radical reactions were activated with a readily available household compact fluorescent lamp (CFL) using a simple flow reactor design based on transparent fluorinated ethylene polymer (FEP) tubing. All of the reactions were carried out using acetonitrile as the solvent, thus avoiding hazardous chlorinated solvents such as CCl4. For each substrate, only 1.05 equiv of NBS was necessary to fully transform the benzylic starting material into the corresponding bromide. The general character of the procedure was demonstrated by brominating a diverse set of 19 substrates containing different functional groups. Good to excellent isolated yields were obtained in all cases. The novel flow protocol can be readily scaled to multigram quantities by operating the reactor for longer time periods (throughput 30 mmol h–1), which is not easily possible in batch photochemical reactors. The bromination protocol can also be performed with equal efficiency in a larger flow reactor utilizing a more powerful lamp. For the bromination of phenylacetone as a model, a productivity of 180 mmol h–1 for the desired bromide was achieved." @default.
• W2334113710 created "2016-06-24" @default.
• W2334113710 creator A5014092019 @default.
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• W2334113710 creator A5058604701 @default.
• W2334113710 creator A5063134639 @default.
• W2334113710 date "2013-11-27" @default.
• W2334113710 modified "2023-10-17" @default.
• W2334113710 title "A Scalable Procedure for Light-Induced Benzylic Brominations in Continuous Flow" @default.
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• W2334113710 doi "https://doi.org/10.1021/jo402409k" @default.
• W2334113710 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24261546" @default.
• W2334113710 hasPublicationYear "2013" @default.
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