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Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor

[Image: see text] Photocatalytic oxidative benzylic bromination with hydrobromic acid (HBr) and hydrogen peroxide (H(2)O(2)) is a green process for the synthesis of benzyl bromides, but suffers from the risk of explosion when performing it in a batch reactor. This disadvantage could be overcome by r...

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Autores principales: Liu, Lin, Liu, Peng, Zhang, Di, Zhang, Hong-Yu, Zhang, Yuecheng, Zhao, Jiquan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8829936/
https://www.ncbi.nlm.nih.gov/pubmed/35155953
http://dx.doi.org/10.1021/acsomega.1c06737
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author Liu, Lin
Liu, Peng
Zhang, Di
Zhang, Hong-Yu
Zhang, Yuecheng
Zhao, Jiquan
author_facet Liu, Lin
Liu, Peng
Zhang, Di
Zhang, Hong-Yu
Zhang, Yuecheng
Zhao, Jiquan
author_sort Liu, Lin
collection PubMed
description [Image: see text] Photocatalytic oxidative benzylic bromination with hydrobromic acid (HBr) and hydrogen peroxide (H(2)O(2)) is a green process for the synthesis of benzyl bromides, but suffers from the risk of explosion when performing it in a batch reactor. This disadvantage could be overcome by running the reaction in a microchannel reactor. In this work, a green and safe process for the synthesis of 2,6-dichlorobenzyl bromide (DCBB) was developed by conducting selective benzylic bromination of 2,6-dichlorotoluene (DCT) with H(2)O(2) as an oxidant and HBr as a bromine source in a microchannel reactor under light irradiation. The reaction parameters were optimized, and the conversion of DCT reached up to 98.1% with a DCBB yield of 91.4% under the optimal reaction conditions.
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spelling pubmed-88299362022-02-11 Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor Liu, Lin Liu, Peng Zhang, Di Zhang, Hong-Yu Zhang, Yuecheng Zhao, Jiquan ACS Omega [Image: see text] Photocatalytic oxidative benzylic bromination with hydrobromic acid (HBr) and hydrogen peroxide (H(2)O(2)) is a green process for the synthesis of benzyl bromides, but suffers from the risk of explosion when performing it in a batch reactor. This disadvantage could be overcome by running the reaction in a microchannel reactor. In this work, a green and safe process for the synthesis of 2,6-dichlorobenzyl bromide (DCBB) was developed by conducting selective benzylic bromination of 2,6-dichlorotoluene (DCT) with H(2)O(2) as an oxidant and HBr as a bromine source in a microchannel reactor under light irradiation. The reaction parameters were optimized, and the conversion of DCT reached up to 98.1% with a DCBB yield of 91.4% under the optimal reaction conditions. American Chemical Society 2022-01-26 /pmc/articles/PMC8829936/ /pubmed/35155953 http://dx.doi.org/10.1021/acsomega.1c06737 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Liu, Lin
Liu, Peng
Zhang, Di
Zhang, Hong-Yu
Zhang, Yuecheng
Zhao, Jiquan
Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor
title Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor
title_full Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor
title_fullStr Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor
title_full_unstemmed Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor
title_short Photocatalytic Oxidative Bromination of 2,6-Dichlorotoluene to 2,6-Dichlorobenzyl Bromide in a Microchannel Reactor
title_sort photocatalytic oxidative bromination of 2,6-dichlorotoluene to 2,6-dichlorobenzyl bromide in a microchannel reactor
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8829936/
https://www.ncbi.nlm.nih.gov/pubmed/35155953
http://dx.doi.org/10.1021/acsomega.1c06737
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