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Issue 6, 2019
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Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

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Abstract

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space–time-yield of 1.27 kg L−1 h−1.

Graphical abstract: Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

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Article information


Submitted
08 Jan 2019
Accepted
22 Jan 2019
First published
22 Jan 2019

This article is Open Access

Org. Biomol. Chem., 2019,17, 1384-1388
Article type
Communication

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

Y. Otake, J. D. Williams, J. A. Rincón, O. de Frutos, C. Mateos and C. O. Kappe, Org. Biomol. Chem., 2019, 17, 1384
DOI: 10.1039/C9OB00044E

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