反应详情

温度

65 °C

To a solution of 4-(5-bromo-2-fluoro-benzyl)-phenol (1.1 g, 3.9 mmol) and cesium carbonate (1.91 g, 5.87 mmol) in N,N-dimethylformamide (15.0 mL) at room temperature was added a solution of toluene-4-sulfonic acid oxetan-3-yl ester (1.34 g, 8.0 mmol) in N,N-dimethylformamide (10.0 mL). The reaction mixture was then stirred overnight at 65° C. After a total of 18 hours, the reaction mixture was cooled to room temperature, diluted with brine and extracted 3 times with ethyl acetate. The combined organic layers were washed twice with water and once with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30% ethyl acetate in heptane to afford 0.948 g (72% yield) of the desired product as a white solid.

1. temperatureAfter a total of 18 hours, the reaction mixture was cooled to room temperature
2. extractionextracted 3 times with ethyl acetate
3. washThe combined organic layers were washed twice with water and once with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude residue was purified by flash chromatography over silica gel eluting with a gradient of 0 to 30% ethyl acetate in heptane