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Dichloromethyl lithium: A valuable reagent in organic synthesis handled in continuous flow mode

Hafner, Andreas and Mancino, Valentina and Meisenbach, Mark and Schenkel, Berthold and Sedelmeier, Joerg Mathias (2017) Dichloromethyl lithium: A valuable reagent in organic synthesis handled in continuous flow mode. Dichloromethyl lithium: A valuable reagent in organic synthesis handled in continuous flow mode.

Abstract

A simple and robust procedure for the synthesis and usage of thermally unstable dichloromethyl lithium in continuous flow mode is described. By utilizing residence times in the range of milliseconds for the generation and electrophilic quench of dichloromethyl lithium, the straightforward synthesis of dichloro carbinols and benzylic pinacol esters was realized at reaction temperatures of −30°C whereas typical temperature in traditional batch mode are below −78°C. The excellent purity profile obtained from the flow process allows to directly telescope the exiting flow stream into semi-batch quenches for further modifications. All transformations gave the desired product in remarkable purity and yield on multigram scale without the necessity for any chromatography.

Item Type: Article
Date Deposited: 08 Feb 2017 00:45
Last Modified: 08 Feb 2017 00:45
URI: https://oak.novartis.com/id/eprint/31745

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