Water → HCID 19744232, compound

Participants

Reaction Conditions

Reaction Steps

6.97 Grams of 3-fluoro-4-(1',1',2',2'-tetrafluoroethoxy)nitrobenzene [i.e. the nitro compound (X) containing fluorine as the substituted X] was dissolved in a mixed solvent of 25 ml of ethyl acetate and 25 ml of acetic acid. The resulting solution was slowly added dropwise to a suspension of 9.0 g of iron powders in a mixed solution of 5 ml of acetic acid and 30 ml of water while maintaining the temperature at 40° C. Thereafter, stirring was continued for 30 minutes at 40° C. to 70° 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 5.35 g of 3-fluoro-4-(1',1',2',2'-tetrafluoroethoxy)aniline [i.e. the aniline compound (IX) containing fluorine as the substituted X]. 1H-NMR (CDCl3): δ(ppm) 6.90-7.30(1H, m), 6.30-6.60(2H), 5.95(1H, tt, J=53, 3 Hz), 3.75(2H, broad)

Provenance & Evidence