As demonstrated elegenantly by Hedrick, BMPCL [γ-(2-bromo-2-methylpropionyl)-ε-caprolactone] can be used to construct block copolymers, expanding the possibilities of dual living polymerizations (consecutive or concurrent) to create new molecular architectures.. This has led to extensive use since it was first reported with at least 16 publications citing its synthesis, despite a ~17% yield over three steps.  The Getzler lab group has worked to optimize a synthesis for BMPCL. This has improved upon the previous protocol by creating a one-column, three step synthesis. The first step is an acylation, followed by a workup. Then, an oxidation of the alcohol to a ketone, followed by another workup. Finally, the ketone is oxidized to an ester, followed by a workup and the sole instance of flash column chromatography. With one column as opposed to three, the process has a lower environmental impact by reducing silica and solvent use. The synthesis is also less toxic as it avoids chromium oxidizing agents and their harsh conditions in favor of a milder process with higher yield. We hope that this improved synthesis will be of broad utility to the polymer community.

Efficient synthesis of BMPCL [γ-(2-bromo-2-methylpropionyl)-ε-caprolactone] inimer

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ACS Fall 2022

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