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

HRID 1061815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1061815
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%). δH (400 MHz, CDCl3) 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); 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-ff2b92eaac584799b5ca50977734b7e7
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960598B2

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