2-AMINO-4,4'-DICHLORODIPHENYL ETHER | CAS 121-27-7

135-12-6

121-27-7

4,4'-Dichloro-2-nitro-diphenyl ether (12.0 g, 42.2 mmol) was used as a raw material, which was mixed with FeCl3 (702 mg, 4.33 mmol) and activated charcoal (3.70 g) in MeOH (360 mL) and stirred at 50 °C. Hydrazine monohydrate (7.00 mL, 144 mmol) was added slowly over 10 minutes, followed by heating the reaction mixture to reflux and stirring for 1 hour. After completion of the reaction, the mixture was cooled, filtered through diatomaceous earth and the filter cake was washed with MeOH. The filtrate was concentrated under reduced pressure to give an oily residue. This residue was dissolved with EtOAc, and the organic layer was washed sequentially with saturated aqueous NaHCO3 and brine, and then dried with Na2SO4. After filtration to remove the insoluble matter, the filtrate was concentrated under reduced pressure to give 5-chloro-2-(4-chlorophenoxy)-aniline (8) (10.6 g, 99% yield) as a colorless solid with a melting point of 59-61 °C. The product was characterized by 1H NMR (400 MHz, CDCl3), 13C NMR (100 MHz, CDCl3) and LC-MS (ESI) to confirm its structure.