Hydrogen Bromide → 1-(Bromomethyl)-4-ethylbenzene

Participants

Reaction Steps

A mixture of 2.72 g (20.0 mmol) of 4-ethylbenzyl alcohol (purchased from Aldrich) and 50 ml of 47% hydrobromic acid (purchased from Wako Junyaku Kogyo) was stirred at room temperature for 30 minutes vigorously and extracted with hexane to give 3.98 g of 4-ethylbenzyl bromide as a colorless oil. Subsequently, to a solution of 1.96 g (40.0 mmol) of sodium cyanide (purchased from Kokusan Kagaku) in 20 ml of dimethyl sulfoxide (purchased from Aldrich) heated at 50 ° C. was added 3.98 g of the above 4-ethylbenzylbromide, the solution was stirred at ambient temperature for 3 hours, the resultant reaction mass was dissolved in water and extracted with hexane, and hexane was removed to give 2.70 g (yield: 93.1%) of 4-ethylphenylacetonitrile as a light yellow oil.

Provenance & Evidence