Reaction #3114

Reaction equation

4-Nitrophenol

sodium chlorodifluoroacetate

sodium hydroxide

→

title compound

Yield 73.4%

4-difluoromethoxynitrobenzene

Yield 73.4%

Solvents

DMF

water

Conditions

Workup

1. 1
   Temperaturethe mixture was cooled to RT
2. 2
   Extractionwas extracted twice with ether
3. 3
   WashThe combined organic extracts were washed twice with brine
4. 4
   Dryingwere dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes )

Procedure

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.

Source