Potassium Carbonate → 4-(5-Chloro-pyridin-2-yl)-phenol

HRID 2060242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060242
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 276852,5-DichloropyridineHCID 27343604-Hydroxyphenylboronic acid

Produkt 1

HCID 1361461364-(5-Chloro-pyridin-2-yl)-phenolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Palladium(0),tetrakis(triphenylphosphine) (4.69 g, 4.05 mmol) was added to a stirred suspension of 2,5-dichloropyridine (12.0 g, 81.08 mmol), 4-hydroxybenzene boronic acid (11.2 g, 81.1 mmol) and potassium carbonate (11.2 g, 81.1 mmol) in dioxane (100 mL) and water (100 mL). The mixture was refluxed for 2 hours, then partitioned between diethyl ether (100 mL) and water (100 mL). The organics were washed with brine (100 mL), dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with 4% methanol in dichloromethane, to afford the title compound as an off-white solid (15.5 g, 81%).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hours
  2. custompartitioned between diethyl ether (100 mL) and water (100 mL)
  3. washThe organics were washed with brine (100 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with 4% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-786a8e5590154eedacf5a19cf85843c5
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278343B2

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