Réaction #3113

Équation de réaction

ethyl acetate

4-Cyanophenol

sodium chlorodifluoroacetate

sodium hydroxide

→

title compound

Rendement 41.0%

4-difluoromethoxybenzonitrile

Rendement 41.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Lavagethe organic layer was washed twice with brine
2. 2
   ExtractionThe organic extract
3. 3
   Séchagewas dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated
6. 6
   AutreThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)
7. 7
   Autreto provide a white solid
8. 8
   Autre(1 mm Hg, 23° C.)

Mode opératoire

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.

Source