1-Chloro-5-methoxy-4-nitro-2-(trifluoromethyl)benzene → 4-Chloro-2-methoxy-5-(trifluoromethyl)aniline

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Reaction Steps

1-Chloro-5-methoxy-4-nitro-2-(trifluoromethyl)benzene (306 mg, 1.19 mmol) was dissolved in acetic acid (5 mL). Iron (436 mg, 7.78 mmol) was added and the mixture was heated under reflux for 1.5 hour. After cooling to room temperature, the mixture was filtered through celite. The filtrate was concentrated under reduced pressure and the residue was taken up in EtOAc. The solution was washed with saturated NaHCO3 (aqueous) and brine, and then dried over MgSO4. Evaporation of the solvent in vacuo afforded an oily residue which was purified by flash chromatography on silica gel (cyclohexane-EtOAc, 7:3) to afford the title compound (177 mg, 66%) as a yellow oil (Rf 0.45, cyclohexane-EtOAc, 7:3). 1H-NMR (δ, ppm, DMSO-d6): 3.85 (s, 3H, CH3—O), 5.27 (bs, 2H, NH2), 7.02 (s, 2H, Harom). LC-MS (m/z): 226 (M+H, 100).

Provenance & Evidence