反応 #52328

反応方程式

3,5-dibromopyridine

sodium hydride

2,2,2-trifluoroethanol

→

title compound

収率 46.0%

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

収率 46.0%

溶媒

DMF

water

DMF

反応条件

後処理

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

実験手順

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).

出典