Water → HCID 19744233, compound

Participants

Reaction Steps

10.5 Grams of 5-bromo-2-nitro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the o-nitroaniline compound (VI) containing bromine as the substituent X] was dissolved in a mixed solvent of 25 ml of ethyl acetate and 25 ml of acetic acid. The resulting solution was dropwise added to a suspension of 5.0 g of iron powders in a mixed solution of 7 ml of acetic acid and 50 ml of water while maintaining the temperature at 45°-70° C. Thereafter, stirring was continued for 10 minutes within the same temperature range. The reaction solution was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydrogencarbonate solution and water in this order, dried over anhydrous magnesium sulfate and concentrated to obtain 9.5 g of 4-bromo-5-(1',1',2',2'-tetrafluoroethoxy) -1,2-benzenediamine. 1H-NMR (CDCl3): δ(ppm) 6.78(1H, s), 6.60(1H), 5.90(1H, tt, J=3, 52 Hz), 3.45(4H, broad)

Provenance & Evidence