Реакция #43336

Уравнение реакции

4-fluorophenol

potassium carbonate

(2-chloro-4-pyridinyl)methanol

Triethylamine

methanesulfonyl chloride

→

title compound

Выход 51.0%

2-chloro-4-[(4-fluorophenoxy)methyl]pyridine

Выход 51.0%

Растворители

ethyl acetate

N,N-dimethylformamide

ethyl acetate

Условия реакции

Обработка

1. 1
   Температураunder cooling with ice
2. 2
   ФильтрацияFiltering
3. 3
   Другоеthe reaction liquid
4. 4
   Концентрированиеthe filtrate was concentrated
5. 5
   workup.WAITs at 80° C. for 20 hours
6. 6
   ТемператураCooling
7. 7
   Другоеthe reaction liquid to room temperature
8. 8
   Промывкаby washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine
9. 9
   Сушкаdrying over anhydrous sodium sulfate
10. 10
    КонцентрированиеConcentrating the solvent under reduced pressure
11. 11
    Другоеthe residue was purified on silica gel column chromatography (KP-Sil, FLASH 40+M, chloroform)

Методика

Triethylamine (1.2 mL, 8.4 mmols) was added to a mixture of (2-chloro-4-pyridinyl)methanol (1.0 g, 7.0 mmols), methanesulfonyl chloride (0.6 mL, 7.7 mmols) and ethyl acetate (20 mL) under cooling with ice, and stirred at room temperature for 2 hours. Filtering the reaction liquid, the filtrate was concentrated. To the resulting residue, 4-fluorophenol (0.94 g, 8.4 mmols), potassium carbonate (1.93 g, 14.0 mmols) and N,N-dimethylformamide (20 mL) were added and s at 80° C. for 20 hours. Cooling the reaction liquid to room temperature, ethyl acetate was added thereto, followed by washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine and drying over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (KP-Sil, FLASH 40+M, chloroform) to provide the title compound (845 mg, 51%).

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