Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: the PIDA–AlBr3 system. Issue 32 (15th May 2018)

• Record Type: Journal Article
• Authors: Satkar, Yuvraj; Ramadoss, Velayudham; Nahide, Pradip D.; García-Medina, Ernesto; Juárez-Ornelas, Kevin A.; Alonso-Castro, Angel J.; Chávez-Rivera, Ruben; Jiménez-Halla, J. Oscar C.; Solorio-Alvarado, César R.
• Is Part Of: RSC advances. Volume 8:Issue 32(2018)
• Page Start: 17806
• Page End: 17812
• Publication Date: 2018-05-15
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c8ra02982b
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A practical electrophilic bromination procedure for the phenolic core was developed under efficient and very mild reaction conditions. The new I(iii)-based brominating reagentPhIOAcBr operationally easy to prepare by mixing PIDA and AlBr3 was used. Abstract : 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 reagentPhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3 . 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.