Evaluation of a Continuous-Flow Photo-Bromination Using N-Bromosuccinimide for Use in Chemical Manufacture

Matthew Waterford; Simon Saubern; Christian H. Hornung

doi:10.1071/CH20372

RESEARCH ARTICLE (Open Access)

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Evaluation of a Continuous-Flow Photo-Bromination Using N-Bromosuccinimide for Use in Chemical Manufacture

Matthew Waterford ^A ^B , Simon Saubern

^A and Christian H. Hornung

^A

+ Author Affiliations

- Author Affiliations

^A CSIRO Manufacturing, Bag 10, Clayton South, Vic. 3169, Australia.

^B Corresponding author. Email: matthew.waterford@csiro.au

Australian Journal of Chemistry 74(8) 569-573 https://doi.org/10.1071/CH20372
Submitted: 21 December 2020 Accepted: 22 March 2021 Published: 9 April 2021

Journal Compilation © CSIRO 2021 Open Access CC BY

Abstract

A continuous-flow photo-bromination reaction on benzyl and phenyl groups was conducted using N-bromosuccinimide as the bromine source inside a preparatory-scale glass plate reactor. This flow reactor system was capable of independently controlling light intensity, wavelength, and reaction temperature, hence exerting an exceptional level of control over the reaction. A short optimisation study for the synthesis of 2-bromomethyl-4-trifluoromethoxyphenylboronic acid pinacol ester resulted in best conditions of 20°C and 10 min residence time using an LED (light-emitting diode) array at 405 nm and acetonitrile as the solvent. The present study evaluates the potential for this easy-to-handle bromination system to be scaled up for chemical manufacture inside a continuous-flow glass plate reactor. The combination with an in-line continuous flow liquid–liquid extraction and separation system, using a membrane separator, demonstrates the potential for continuous flow reaction with purification in an integrated multi-stage operation with minimal manual handling in between.

Keywords: continuous flow chemistry, photochemistry, photo-bromination, microreactor, in-line separation, photoactivation.

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