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

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 bromina...

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Main Authors:	Reinout Van Kerrebroeck, Pieter Naert, Thomas S. A. Heugebaert, Matthias D’hooghe, Christian V. Stevens
Format:	Article
Language:	English
Published:	MDPI AG 2019-06-01
Series:	Molecules
Subjects:	aromatic substitution bromination C–H activation ionic liquids microreactors
Online Access:	https://www.mdpi.com/1420-3049/24/11/2116

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record_format	Article
spelling	doaj-ff04885c58bf46f4b1b5df17b54819cc2020-11-25T01:14:52ZengMDPI AGMolecules1420-30492019-06-012411211610.3390/molecules24112116molecules24112116Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in BatchReinout Van Kerrebroeck0Pieter Naert1Thomas S. A. Heugebaert2Matthias D’hooghe3Christian V. Stevens4SynBioC research Group, Department of Green Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, BelgiumSynBioC research Group, Department of Green Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, BelgiumSynBioC research Group, Department of Green Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, BelgiumSynBioC research Group, Department of Green Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, BelgiumSynBioC research Group, Department of Green Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, BelgiumBromination 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 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.https://www.mdpi.com/1420-3049/24/11/2116aromatic substitutionbrominationC–H activationionic liquidsmicroreactors
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Reinout Van Kerrebroeck Pieter Naert Thomas S. A. Heugebaert Matthias D’hooghe Christian V. Stevens
spellingShingle	Reinout Van Kerrebroeck Pieter Naert Thomas S. A. Heugebaert Matthias D’hooghe Christian V. Stevens Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch Molecules aromatic substitution bromination C–H activation ionic liquids microreactors
author_facet	Reinout Van Kerrebroeck Pieter Naert Thomas S. A. Heugebaert Matthias D’hooghe Christian V. Stevens
author_sort	Reinout Van Kerrebroeck
title	Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
title_short	Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
title_full	Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
title_fullStr	Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
title_full_unstemmed	Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch
title_sort	electrophilic bromination in flow: a safe and sustainable alternative to the use of molecular bromine in batch
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2019-06-01
description	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 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.
topic	aromatic substitution bromination C–H activation ionic liquids microreactors
url	https://www.mdpi.com/1420-3049/24/11/2116
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Electrophilic Bromination in Flow: A Safe and Sustainable Alternative to the Use of Molecular Bromine in Batch

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