Borane → 11-Bromo-1-undecanol

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Reaction Steps

A 250 ml. of solution of 1 M borane in tetrahydrofuran is cooled in an ice-water bath, and to this is slowly added 50 g. 11-bromoundecanoic acid in 150 ml. dry tetrahydrofuran. After stirring at room temperature for 19 hours the reaction is quenched by the addition of 300 ml. 10% hydrochloric acid. The aqueous solution is extracted three times with 150 ml. portions of ether, the organic layers are combined, washed with saturated brine, dried with anhydrous magnesium sulfate and evaporated. Distillation of the residue yields 11-bromoundecanol as a colorless liquid.

Provenance & Evidence