Reaction #3115

Reaction equation

ethyl acetate

4-Cyanophenol

methyl chlorodifluoroacetate

potassium carbonate

→

title compound

Yield 53.2%

4-difluoromethoxybenzonitrile

Yield 53.2%

Solvents

DMF

Conditions

Workup

1. 1
   Washthe organic layer was washed twice with 10% NaOH
2. 2
   ExtractionThe organic extract
3. 3
   Dryingwas dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Otherevaporated
6. 6
   OtherThe residue was purified by flash chromatography (silica gel, 20% ether/hexanes)

Procedure

4-Cyanophenol (0.12 G, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 75°-80° C. for 0.3 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organic layer was washed twice with 10% NaOH. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 20% ether/hexanes) to provide the title compound as a colorless solid (0.09 g, 53%). mp 34°-35° C.

Source