Hydrochloric Acid → 4-(1-Aminocyclopropyl)benzonitrile

Participants

Reaction Steps

To a solution of terephthalonitrile (3.30 g, 25.8 mmol.) in dichloromethane (130 ml), Titanium (IV) isopropoxide (7.6 ml, 25.8 mmol) was added at room temperature followed by dropwise addition of ethyl magnesium bromide 1M in diethyl ether (47.0 ml). The mixture was stirred at room temperature for 45 min, then boron trifluoride etherate (5 ml) was added at once. After 2 hours, HCl aqueous solution (5%) was added to quench the reaction. The aqueous phase was separated, basified with aqueous 1M NaOH and extracted with ethylacetate. The organic phase was dried over Na2SO4 and concentrated under vacuo. The residue was purified by column chromatography eluting with a mixture petroleum ether/ethyl acetate (5:1). Collected fractions after solvent evaporation afforded the title compound (D14) (500 mg) as a white solid.

Provenance & Evidence