1,4-Dioxane → 2-(2-Fluoro-5-nitrophenyl)pyridine

HRID 13286

Reaktionsgleichung

Reaktionsgleichung von HRID 13286
Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].C(=O)(O)[O-].[Na+].O1[CH2:22][CH2:21]OCC1>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]=1[C:22]1[CH:21]=[CH:2][CH:3]=[CH:4][N:9]=1

Komponenten

4

Edukt 3

HCID 312751,4-DioxaneHCID 696992-Bromo-1-fluoro-4-nitrobenzeneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 222853002-(2-Fluoro-5-nitrophenyl)pyridine

Versuchsvorschrift

0.55 g of Tetrakis-triphenylphosphine palladium was added to a 1,4-dioxane (20 ml) solution of 2.1 g of 3-bromo-4-fluoro-nitrobenzene and 2.3 g of 2-trimethyltin-pyridine, and the reaction liquid was heated overnight under reflux. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=7/1) to obtain the entitled compound as a yellow solid.

Aufarbeitung

  1. customthe reaction liquid
  2. temperaturewas heated overnight
  3. temperatureunder reflux
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe solvent was evaporated away under reduced pressure
  8. customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=7/1)

Quellen und Nachweise

ORD-Eintrag
ord-b06ca7ffde7348cc9499a39a52f86f8f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728025B2

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