Toluene → 3-(Pyridin-2-yl)benzaldehyde

HRID 78043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 78043
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C1(C)C=CC=CC=1.C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)CCC.[F-].[K+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.O>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 765833-BromobenzaldehydeHCID 522689Potassium FluorideHCID 6077842-(Tributylstannyl)pyridine

Produkt 1

HCID 37100393-(Pyridin-2-yl)benzaldehydeAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 3-bromobenzaldehyde (930 mg, 5.0 mmol) and toluene (10 mL) were added tri-n-butyl (2-pyridyl) tin (2.1 g, 5.6 mmol) and bis(triphenylphosphine) palladium (II) chloride (350 mg, 0.50 mmol), and the reaction mixture was refluxed for 5 hours. The reaction mixture was cooled to room temperature, and saturated aqueous potassium fluoride solution (1 mL) was added at that temperature and stirred for 30 minutes at room temperature. Water and ethyl acetate were added to the reaction mixture, which was then filtered through a Celite pad. The organic layer of the filtrate was separated and washed with saturated aqueous sodium chloride. The solvent was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (530 mg, 58%).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. filtrationwas then filtered through a Celite pad
  3. customThe organic layer of the filtrate was separated
  4. washwashed with saturated aqueous sodium chloride
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-40be818df0ea412e927ae95e2f61720c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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