Hydrochloric Acid → 4-(Bromomethyl)benzeneethanol

Participants

Reaction Conditions

Reaction Steps

3.85 g (18.81 mmol) of 4-bromomethylphenylacetic acid are dissolved in 150 ml of THF, and 20 ml of a 1M solution of BH3 in THF is added slowly with stirring, at 0° C. The reaction mixture is then slowly warmed to room temperature and stirred overnight at room temperature. 2M hydrochloric acid is added, and the reaction mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and concentrated. 3.64 g (16.92 mmol) of the 2-[4-(bromomethyl)phenyl]ethanol thus obtained are, without further purification, dissolved in 36 ml of DMSO, and 1.65 g (25.38 mmol) of potassium cyanide are added. The reaction mixture is stirred at room temperature for 1 h and then poured into diethyl ether/sat. aqueous sodium bicarbonate solution. The organic phase is washed three times with water, dried over magnesium sulfate, filtered and concentrated. This gives 2.5 g of product.

Provenance & Evidence