4-Vinylpyridine → 4-[2-(4-Nitro-phenyl)-vinyl]-pyridine

HRID 1514301

Reaktionsgleichung

Reaktionsgleichung von HRID 1514301
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[CH2:12]>CC([O-])=O.CC([O-])=O.[Pd+2].CC#N>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[CH:11][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 2

HCID 75024-VinylpyridineHCID 124951-Iodo-4-nitrobenzene

Produkt 1

HCID 3071364-[2-(4-Nitro-phenyl)-vinyl]-pyridineAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a CH3CN solution of 1-iodo-4-nitrobenzene (498 mg, 2 mmol) and 4-vinylpyridine (262 mg, 2.5 mmol) was added TEA (350 μL, 2.5 mmol) and Pd(OAc)2 (0.45 mg, 0.2 mmol). The mixture was heated to 100° C. for 48 hr in a capped Pyrex tube. It was then cooled to room temperature, quenched with 1N HCl (20 mL) and concentrated under reduced pressure. The mixture was filtered and the solid was taken up in EtOAc (30 mL) and washed with 1N NaOH (30 mL). The organic layer was concentrated, dried over Na2SO4 and concentrated to give 4-[2-(4-nitro-phenyl)-vinyl]-pyridine as yellow solid (160 mg, 37%).

Aufarbeitung

  1. temperatureIt was then cooled to room temperature
  2. customquenched with 1N HCl (20 mL)
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe mixture was filtered
  5. washwashed with 1N NaOH (30 mL)
  6. concentrationThe organic layer was concentrated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c79662639e1b418a96e38104c4b3c123
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222249B2

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