反应 #52328

反应方程式

3,5-dibromopyridine

sodium hydride

2,2,2-trifluoroethanol

→

title compound

收率 46.0%

3-Bromo-5-(2,2,2-trifluoro-ethoxy)-pyridine

收率 46.0%

溶剂

DMF

water

DMF

反应条件

后处理

1. 1
   温度After cooling to room temperature
2. 2
   萃取extracted with ethyl acetate
3. 3
   干燥The extracts were dried over magnesium sulfate
4. 4
   其他the solvent was removed under reduced pressure
5. 5
   其他The crude product was chromatographed on silica (5% ethyl acetate/hexanes)

实验过程

To a slurry of sodium hydride (60% dispersion in mineral oil, 0.54 g, 14 mmol) in DMF (15 mL) was added commercially available 2,2,2-trifluoroethanol (0.97 mL, 14 mmol) at room temperature. After stirring for 15 minutes, a solution of 3,5-dibromopyridine (3.2 g, 14 mmol) in 5 mL of DMF was added dropwise. The reaction mixture was heated overnight at 70° C. After cooling to room temperature, the reaction was diluted with water and extracted with ethyl acetate. The extracts were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (5% ethyl acetate/hexanes) to give the title compound (1.6 g, 46% yield) as clear oil. 1H NMR (CDCl3) δ 8.42 (d, 1H, J=1.7 Hz), 8.32 (d, 1H, J=2.5 Hz), 7.46 (m, 1H), 4.42 (m, 2H).

来源