반응 #52328

반응 방정식

3,5-dibromopyridine

sodium hydride

2,2,2-trifluoroethanol

→

title compound

수율 46.0%

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

수율 46.0%

용매

DMF

water

DMF

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   추출extracted with ethyl acetate
3. 3
   건조The extracts were dried over magnesium sulfate
4. 4
   기타the solvent was removed under reduced pressure
5. 5
   기타The crude product was chromatographed on silica (5% ethyl acetate/hexanes)

실험 절차

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).

출처