Hydrochloric Acid → 1-[4-(Trifluoromethoxy)phenyl]cyclopropan-1-amine

Participants

Reaction Steps

Ethylmagnesium bromide (3.0 M in diethyl ether, 7.33 ml, 22.0 mmol) was added over 50 minutes to a solution of 4-(trifluoromethoxy)benzonitrile (1.87 g, 10.0 mmol) and tetraisopropoxytitanium (3.22 ml, 11.0 mmol) in diethyl ether (50 ml) at −70° C., and the whole was stirred at room temperature for 1 hour. Boranetrifluoride diethyl ether complex (2.53 ml, 20.0 mmol) was added over 15 minutes to the reaction mixture and the whole was stirred at room temperature for 3 hours. 1N aqueous HCl solution (30 ml) and diethyl ether (90 ml) were added to the reaction mixture, and the whole was poured into aqueous 10% NaOH solution (100 ml), extracted with diethyl ether (150 ml×2), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate/hexane: 55/45 to 75/25) to give 1-(4-(trifluoromethoxy)phenyl)cyclopropanamine (1.38 g, 63%).

Provenance & Evidence