2-Bromo-1-fluoro-4-nitrobenzene → 2-(2-Fluoro-5-nitrophenyl)pyridine

HRID 586252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586252
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[F:11].CCCC[Sn]([C:25]1[N:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(CCCC)CCCC>C1COCC1.CN(C=O)C>[F:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:29]1[CH:28]=[CH:27][CH:26]=[CH:25][N:30]=1

Komponenten

5

Edukt 2

HCID 696992-Bromo-1-fluoro-4-nitrobenzene2×HCID 6077842-(Tributylstannyl)pyridine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-1-fluoro-4-nitrobenzene (2.0 g, 9.1 mmol) and 2-(1,1,1-tributylstannyl)pyridine (3.36 g, 9.11 mmol) in THF (80 ml) and DMF (10 ml) was degassed with nitrogen. [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (200 mg, 3 mol %) was added, and the mixture was heated at reflux for 24 h. More 2-bromo-1-fluoro-4-nitrobenzene (0.60 g, 2.7 mmol) and catalyst (100 mg, 1.5 mol %) were added, and the mixture was heated as before for another 24 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with 50% dichloromethane in isohexane, then 100% dichloromethane, then 100% ethyl acetate (UV detection). 2-(2-Fluoro-5-nitrophenyl)pyridine was isolated as a colourless solid (2.11 g, 100%): 1H NMR (400 MHz, CDCl3) δ 7.30-7.37 (2H, m), 7.80-7.87 (2H, m), 8.27 (1H, m), 8.78 (1H, m), 9.01 (1H, dd, J 3.1, 6.7 Hz); MS (ES+) m/z 219 [M+H]+.

Aufarbeitung

  1. customwas degassed with nitrogen
  2. addition[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (200 mg, 3 mol %) was added
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 24 h
  5. temperaturethe mixture was heated as before for another 24 h
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography on silica gel
  8. washeluting with 50% dichloromethane in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-3d7b8c3d3c3d4c398144a816d9c12170
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936608B2

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