Реакция #3113

Уравнение реакции

ethyl acetate

4-Cyanophenol

sodium chlorodifluoroacetate

sodium hydroxide

→

title compound

Выход 41.0%

4-difluoromethoxybenzonitrile

Выход 41.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Промывкаthe organic layer was washed twice with brine
2. 2
   ЭкстракцияThe organic extract
3. 3
   Сушкаwas dried (MgSO4)
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated
6. 6
   ДругоеThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)
7. 7
   Другоеto provide a white solid
8. 8
   Другое(1 mm Hg, 23° C.)

Методика

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.

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