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Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: the PIDA–AlBr~3~ system† by Yuvraj Satkar; Velayudham Ramadoss; Pradip D. Nahide; Ernesto García-Medina; Kevin A. Juárez-Ornelas; Angel J. Alonso-Castro; Ruben Chávez-Rivera; J. Oscar C. Jiménez-Halla; César R. Solorio-Alvarado is a Materials Science article available to read on EtoBox.

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A practical electrophilic bromination procedure for phenols and phenol–ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr~3~. Our DFT calculations suggest that this is likely the brominating active species, which is prepared __in situ__ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.

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Author

Yuvraj Satkar; Velayudham Ramadoss; Pradip D. Nahide; Ernesto García-Medina; Kevin A. Juárez-Ornelas; Angel J. Alonso-Castro; Ruben Chávez-Rivera; J. Oscar C. Jiménez-Halla; César R. Solorio-Alvarado

Publisher

The Royal Society of Chemistry

Published

2018

Language

EN

Field

Materials Science (Physical Sciences)