2,2,2-Trifluoroethanol → 3-Bromo-5-(2,2,2-trifluoroethoxy)pyridine

HRID 1295188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295188
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1>CN(C=O)C.O>[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([O:6][CH2:5][C:4]([F:8])([F:7])[F:3])[CH:15]=1

Komponenten

6

Edukt 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

Produkt 1

HCID 225703523-Bromo-5-(2,2,2-trifluoroethoxy)pyridineAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was chromatographed on silica (5% ethyl. acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-38dd584f9604458199d01c96ee3e0489
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241789B2

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