Sodium Hydroxide → 2-(5-Fluoro-2-{[4'-(trifluoromethyl)-1,1'-biphenyl-4-yl]methoxy}phenyl)ethylamine

Participants

Reaction Conditions

Reaction Steps

140.97 g (0.366 mol) of (5-fluoro-2-{[4′-(trifluoromethyl)-1,1′-biphenyl-4-yl]methoxy}phenyl)-acetonitrile are dissolved in 701 ml of anhydrous THF under argon and, after cooling to 0° C., 361.6 ml (0.362 mol) of a 1 M solution of lithium aluminum hydride in THF are added. Then 73.2 g (0.55 mol) of aluminum trichloride in 701 ml of THF are slowly added dropwise to the reaction solution. The reaction mixture is stirred at room temperature for 3.5 h. After reaction is complete, the solution is cooled to 0° C. and aqueous sodium hydroxide solution is slowly added. The aqueous phase is extracted three times with ethyl acetate, and the combined organic phases are dried over sodium sulfate, filtered and concentrated to dryness in vacuo. The crude product is purified by chromatography on 10 kg of silica gel (mobile phase: dichloromethane/methanol 6:4). 90.28 g (61% of theory) of the title compound are obtained.

Provenance & Evidence