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

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).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 1.5 hour
3. filtrationthe mixture was filtered through celite
4. concentrationThe filtrate was concentrated under reduced pressure
5. washThe solution was washed with saturated NaHCO3 (aqueous) and brine
6. dry with materialdried over MgSO4
7. customEvaporation of the solvent in vacuo
8. customafforded an oily residue which
9. customwas purified by flash chromatography on silica gel (cyclohexane-EtOAc, 7:3)

ORD record

ord-82e2abf6944549e3a92c54e62427b8a0

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625922B2