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ChemicalBook CAS DataBase List 1-CHLORO-5-METHOXY-4-NITRO-2-(TRIFLUOROMETHYL)BENZENE
646989-36-8

1-CHLORO-5-METHOXY-4-NITRO-2-(TRIFLUOROMETHYL)BENZENE synthesis

1synthesis methods
1-CHLORO-5-METHOXY-4-NITRO-2-(TRIFLUOROMETHYL)BENZENE

646989-36-8
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4-CHLORO-2-METHOXY-5-(TRIFLUOROMETHYL)-BENZENAMINE

284462-45-9
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Yield:284462-45-9 66%

Reaction Conditions:

with iron;acetic acid for 1.5 h;Heating / reflux;

Steps:

XVIII.128

(XVIII) Synthesis of aromatic amines starting materials; Synthesis 128; 4-Chloro-2-methoxy-5-(trifluoromethyl)benzenamine; 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 sitica 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).

References:

WO2006/43090,2006,A1 Location in patent:Page/Page column 172