Reacción #3115

Ecuación de reacción

ethyl acetate

4-Cyanophenol

methyl chlorodifluoroacetate

potassium carbonate

→

title compound

Rendimiento 53.2%

4-difluoromethoxybenzonitrile

Rendimiento 53.2%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organic layer was washed twice with 10% NaOH
2. 2
   ExtracciónThe organic extract
3. 3
   Secadowas dried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by flash chromatography (silica gel, 20% ether/hexanes)

Procedimiento

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.

Fuente