4-Nitrophenol → 4-(Difluoromethoxy)nitrobenzene

Participants

Reaction Conditions

Reaction Steps

4-Nitrophenol (0.10 g, 0.72 mmol, Aldrich), sodium chlorodifluoroacetate (0.11 g, 0.72 mmol, Alfa Products) and sodium hydroxide (0.03 g, 0.72 mmol) were combined in dry DMF (1 mL) under an atmosphere of argon. After stirring at 125° C. for 1 h, the mixture was cooled to RT, was diluted with water and was extracted twice with ether. The combined organic extracts were washed twice with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes ) to provide the title compound as a white solid (0.10 g, 73%). mp 33°-35° C.

Provenance & Evidence