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

HRID 50558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 50558
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1)=[O:8].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>CO.C1(C)C=CC=CC=1.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH:7]=[O:8]

Komponenten

8

Edukt 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acid

Produkt 1

HCID 37100393-(Pyridin-2-yl)benzaldehydeAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2M aq. Na2CO3 (5 mL) and a solution of 3-formylphenylboronic acid (1.14 g, 7.60 mmol) in methanol (5 mL) were added to a solution of 2-bromopyridine (1.00 g, 6.33 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) in toluene (10 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.03 g (89%) of the title compound. MS 184(M+H)+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a73f22bb93d54387b7760e75850f9d60
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713455B2

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