Ammonium Chloride → 4-[(Prop-2-en-1-yl)oxy]-3-(trifluoromethoxy)aniline

Participants

Reaction Conditions

Reaction Steps

To a solution of NH4Cl (3.3 g, 61.7 mmol) in EtOH (30.0 mL) and H2O (15.0 mL) at 90° C., was added a solution of 1-allyloxy-4-nitro-2-trifluoromethoxybenzene (1.6 g, 6.08 mmol) in THF (5.0 mL) followed by the addition of iron (1.02 g, 17.9 mmol, 3.0 equi) in two portions with 5 minutes interval. The resulting suspension was stirred at 90° C. for two hours then filtered through a pad of celite and the celite washed with EtOAc. The filtrate was diluted with H2O and extracted with EtOAc (3×70 mL). The combined organic layer was washed with aq. Na2CO3 (2×100 mL), brine (200 mL), dried over Na2SO4, and concentrated in vacuo to afford 4-allyloxy-3-trifluoromethoxyaniline (1.6 g). The product was used in the subsequent Step without further purification.

Provenance & Evidence