Reaktion #52328

Reaktionsgleichung

3,5-dibromopyridine

sodium hydride

2,2,2-trifluoroethanol

→

title compound

Ausbeute 46.0%

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

Ausbeute 46.0%

Lösungsmittel

DMF

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   TrocknenThe extracts were dried over magnesium sulfate
4. 4
   Sonstigethe solvent was removed under reduced pressure
5. 5
   SonstigeThe crude product was chromatographed on silica (5% ethyl acetate/hexanes)

Vorschrift

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).

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