4,5-Difluoro-2-nitroaniline → 1,2-Diamino-4,5-difluorobenzene

Participants

Reaction Steps

Into a Parr bottle were placed 4,5-difluoro-2-nitroaniline (5.00 g, 28.72 mmol), platinum (IV) oxide (0.31 g, 1.13 mmol) and methanol (60 mL). The bottle was flushed three times with hydrogen and was finally pressurized to 45 psig with hydrogen. The bottle was shaken for 5 h, after which time it was depressurized and the contents were poured into a separatory funnel containing ethyl acetate (300 mL) and water (300 mL). The organic layer was collected and washed with saturated aqueous brine solution (100 mL), dried over magnesium sulfate and the solvents were removed under reduced pressure using a rotary evaporator to leave 3.37 g (81%) of a brown solid. MS (Cl): m/z 145 (M+1).

Provenance & Evidence