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Merck

Telescoped approach to aryl hydroxymethylation in the synthesis of a key pharmaceutical intermediate.

The Journal of organic chemistry (2013-05-31)
Catherine N Slattery, Rebecca E Deasy, Anita R Maguire, Michael E Kopach, Utpal K Singh, Mark D Argentine, William G Trankle, Roger Brian Scherer, Humphrey Moynihan
RESUMO

An efficient synthetic approach leading to introduction of the hydroxymethyl group to an aryl moiety via combination of the Bouveault formylation and hydride reduction has been optimized using a rational, mechanistic-based approach. This approach enabled telescoping of the two steps into a single efficient process, readily amenable to scaleup.

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2-Bromo-4-fluoroanisole, 96%