Water → 3-Chloro-4-(1',1',2',2'-tetrafluoroethoxy)aniline

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Reaction Conditions

Reaction Steps

12.5 Grams of 3-chloro-4-(1',1',2',2'-tetrafluoroethoxy)nitrobenzene [i.e. the nitro compound (X) containing chlorine as the substituted X] was dissolved in a mixed solvent of 50 ml of ethyl acetate and 50 ml of acetic acid. The resulting solution was slowly added dropwise to a suspension of 12.2 g of iron powders in a mixed solution of 13 ml of acetic acid and 130 ml of water while maintaining the temperature at 40° C. Thereafter, stirring was continued for 30 minutes at 40° C. to 60° C. 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 then with water, dried over anhydrous magnesium sulfate and concentrated. The residue obtained was subjected to column chromatography on silica gel with chloroform as an eluent to obtain 9.41 g of 3-chloro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the aniline compound (IX) containing chlorine as the substituted X]. 1H-NMR (CDCl3): δ(ppm) 7.10(1H, d, J=9 Hz , 6.70(1H, d, J=3 Hz), 6.48(1H, dd, J=9, 3 Hz), 5.95(1H, tt, J=53, 3 Hz), 3.65(2H, broad)

Provenance & Evidence