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Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch.

ABSTRACT: Bromination reactions are crucial in today's chemical industry since the versatility of the formed organobromides makes them suitable building blocks for numerous syntheses. However, the use of the toxic and highly reactive molecular bromine (Br₂) makes these brominations very challenging and hazardous. We describe here a safe and straightforward protocol for bromination in continuous flow. The hazardous Br₂ or KOBr is generated in situ by reacting an oxidant (NaOCl) with HBr or KBr, respectively, which is directly coupled to the bromination reaction and a quench of residual bromine. This protocol was demonstrated by polybrominating both alkenes and aromatic substrates in a wide variety of solvents, with yields ranging from 78% to 99%. The protocol can easily be adapted for the bromination of other substrates in an academic and industrial environment.

SUBMITTER: Van Kerrebroeck R

PROVIDER: S-EPMC6600453 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch.

Van Kerrebroeck Reinout R Naert Pieter P Heugebaert Thomas S A TSA D'hooghe Matthias M Stevens Christian V CV

Molecules (Basel, Switzerland) 20190604 11

Bromination reactions are crucial in today's chemical industry since the versatility of the formed organobromides makes them suitable building blocks for numerous syntheses. However, the use of the toxic and highly reactive molecular bromine (Br<sub>2</sub>) makes these brominations very challenging and hazardous. We describe here a safe and straightforward protocol for bromination in continuous flow. The hazardous Br<sub>2</sub> or KOBr is generated in situ by reacting an oxidant (NaOCl) with H ...[more]

PMID: 31167456

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