2-Chloropyridine → 2-(o-Tolyl)pyridine

HRID 13871

Reaktionsgleichung

Reaktionsgleichung von HRID 13871
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]1([CH3:17])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.[F-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCCC1>[C:8]1([CH3:17])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 79772-ChloropyridineHCID 522689Potassium FluorideHCID 27332672-Methylphenyl boronic acid

Produkt 1

HCID 825102-(o-Tolyl)pyridineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 23136663Tri-tert-butylphosphonium TetraphenylborateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 50-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.568 g (5 mmol) of 2-chloropyridine, 0.748 g (5.5 mmol) of ortho-tolylboronic acid, 0.011 g (0.05 mmol) of palladium (II) acetate, 0.959 g (17 mmol) of potassium fluoride and 10 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.026 g (0.05 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 24 hours. After the completion of the reaction, 10 ml of 10% aqueous sodium hydroxide solution was added, followed by separation. The organic phase was purified by column chromatography to afford 0.711 g of 2-ortho-tolylpyridine (yield: 84 mol % based on 2-chloropyridine). The identification of the product was made by mass spectroscopy.

Aufarbeitung

  1. customA 50-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 25° C. for 24 hours
  5. customAfter the completion of the reaction, 10 ml of 10% aqueous sodium hydroxide solution
  6. additionwas added
  7. customfollowed by separation
  8. customThe organic phase was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-955f98f8f465418587f734f49dc456c1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728176B2

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