Magnesium → 3-Amino-4-cyano-5-(2,2,2-trifluoroethoxy)anisole

Participants

Reaction Steps

3-Azido-4-cyano-5-(2,2,2-trifluoroethoxy)anisole (5.66 g, 0.0208 mol) was added to a suspension of magnesium turnings (1.86 g, 0.0775 mol) in methanol (150 ml) and the reaction stirred at room temperature for 40 hours. The reaction was concentrated under reduced pressure to a minimum volume and ethyl acetate (200 ml) added. The mixture was washed with saturated aqueous ammonium chloride solution (75 ml) and brine (75 ml) and then dried (MgSO4), filtered and evaporated under reduced pressure. Trituration with diethyl ether:hexane gave the subtitle compound as a brown solid (4.51 g, 88%). Rf 0.46 (ethyl acetate:hexane, 1:1, v/v). MS m/z 247 (MH)+.

Provenance & Evidence