Sodium Cyanide → 2-(2-(Methylthio)phenyl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

Phosphorus tribromide (75 g) in toluene (50 ml) was added to a stirred mixture of 2-methylthiobenzyl alcohol (42.5 g) in toluene (25 ml) over 10 minutes at 5° C. The mixture was then stirred at 40° C. for 1 hour, water (100 ml) was added and stirring continued at ambient temperature for 1 hour. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combined organic layers yielded an oil. The oil (58.6 g) was dissolved in a 1:2 mixture of water and ethanol and sodium cyanide (26.5 g) was added over 15 minutes. The mixture was stirred at 50° C. for 1.5 hours then poured onto water (500 ml) and extracted with ethyl acetate. The extract yielded 2-methylthiophenylacetonitrile.

Provenance & Evidence