Reacción #3113

Ecuación de reacción

ethyl acetate

4-Cyanophenol

sodium chlorodifluoroacetate

sodium hydroxide

→

title compound

Rendimiento 41.0%

4-difluoromethoxybenzonitrile

Rendimiento 41.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadothe organic layer was washed twice with brine
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, 25% ethyl acetate/hexanes)
7. 7
   Otroto provide a white solid
8. 8
   Otro(1 mm Hg, 23° C.)

Procedimiento

4-Cyanophenol (0.50 g, 4.2 mmol, Aldrich), sodium chlorodifluoroacetate (0.77 g, 5 mmol, Alfa Products), and sodium hydroxide (0.20 g, 5 mmol) were combined in dry DMF (2 mL) under an atmosphere of argon. After stirring at 125°-130° C. for 5 h, the mixture was cooled to RT, ethyl acetate (50 mL) was added and the organic layer was washed twice with brine. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide a white solid. The solid was sublimed (1 mm Hg, 23° C.) to provide the title compound as colorless crystals (0.29 g, 41%). mp 33°-35° C.

Fuente