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Efficient scale up of photochemical bromination of conjugated allylic compounds in continuous-flow

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Abstract

A continuous-flow process for the bromination of conjugated allylic compounds with N-bromosuccinimide (NBS) is developed. The reaction was optimized in a self-made continuous-flow photoreactor based on a commercially available household lamp. The productivity of this continuous step attains 70.5 g/h under the optimal conditions. Compared to batch-mode synthesis, the conversion rate and selectivity of this flow-mode was significantly improved. In addition, the reaction time could be significantly reduced from a few hours to a few minutes.

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Acknowledgments

We are grateful to the Natural Science Foundation of China (No. 21776254) and Natural Science Foundation of Zhejiang Province (No. LQ20B060006) for financial help.

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Author notes

  1. Jiadi Zhou and Zhi Chen contributed equally to this work.

Authors and Affiliations

  1. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Jiadi Zhou & Jianjun Li

  2. National Engineering Research Center for Process Development of Active Pharmaceutical Ingredients, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Jiadi Zhou & Jianjun Li

  3. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, 310014, People’s Republic of China

    Zhi Chen, Yunfei He, Zhihao Lin, Chaodong Wang, Zhonghui Li & Jianjun Li

Authors
  1. Jiadi Zhou
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  2. Zhi Chen
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  3. Yunfei He
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  4. Zhihao Lin
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Correspondence to Jianjun Li.

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Highlights

Development of conjugated allylic brominations reaction in continuous-flow with high conversion rate, selectivity and productivity.

Optimized the process parameters experiments approach.

Designed a new type of reaction device.

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Zhou, J., Chen, Z., He, Y. et al. Efficient scale up of photochemical bromination of conjugated allylic compounds in continuous-flow. J Flow Chem 11, 127–134 (2021). https://doi.org/10.1007/s41981-020-00116-3

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  • DOI: https://doi.org/10.1007/s41981-020-00116-3

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