반응 #43336

반응 방정식

4-fluorophenol

potassium carbonate

(2-chloro-4-pyridinyl)methanol

Triethylamine

methanesulfonyl chloride

→

title compound

수율 51.0%

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

수율 51.0%

용매

ethyl acetate

N,N-dimethylformamide

ethyl acetate

반응 조건

후처리

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

실험 절차

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%).

출처