Borane → 2-(2-Bromophenyl)ethan-1-ol

Participants

Reaction Steps

To a cooled to 0° C. solution of 10.0 grams (0.0465 mole) of 2-bromophenylacetic acid in 75 milliliters of dry tetrahydrofuran was added dropwise over a one-half hour period, a solution of 0.070 mole of borane in tetrahydrofuran while the reaction mixture was maintained under a nitrogen atmosphere. After completion of the addition, stirring was continued for one hour at ambient temperature, then cooled and the reaction quenched by adding 100 milliliters of water dropwise to the cooled mixture. Thereafter, the mixture was diluted with 100 milliliters of diethyl ether, sodium chloride was added to the resulting mixture and the organic and aqueous phases were mechanically separated. The organic solution was washed with saturated sodium bicarbonate solution and dried over sodium sulfate to obtain a clear, colorless dried solution. The solution was placed on a rotary evaporator to remove the solvent and to obtain 9.11 grams (98 percent) of the desired 2-(2-bromophenyl)ethanol intermediate as a clear oil. The Rf was 0.5 on silica gel when eluted with one percent methanol in chloroform.

Provenance & Evidence