Novel reactions under flow chemistry conditions: Formation of α-bromoketones previously unavailable under batch conditions

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    Using the Vapourtec R-Series flow chemistry system researchers from the Department of Chemistry at the University of Cambridge and the Institut fur Organische Chemie at Leibniz Universitat Hannover have discovered new chemical reactivity patterns under flow conditions that were not previously possible under batch conditions.

    Continuous flow chemistry as a process intensification tool is well known and over the last decade there have been an ever increasing number of publications using continuous flow applications in chemical synthesis. However, its ability to enable chemists to perform reactions which are not possible in batch is less well studied or understood. This paper provides an excellent example of how flow chemistry can help deliver novel materials. Examples like this can only accelerate the worldwide adoption of flow chemistry techniques into the medicinal and discovery chemistry labs.

    The formation of alpha-dibromoketones, useful intermediates in the synthesis of pyrazines, triazines, imidazoles and alkynol ethers, is limited under batch conditions due to the lack of control of reaction conditions. The application of flow techniques allows for the formation of the unstable lithiated dibromomethane species and its immediate reaction on forming to give the desired dibromoketone through better temperature control, mixing and defined reaction times.

    Under continuous flow techniques the authors were able to demonstrate the preparation of various alpha-dibromoketones which could not be obtained in batch experiments.

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