Sodium Carbonate → HCID 18631015, Verbindung

HRID 1059965

Reaktionsgleichung

Reaktionsgleichung von HRID 1059965
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[Pd].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.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>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 47384842-Bromo-4-methoxypyridine

Produkt 1

HCID 18631015HCID 18631015, VerbindungAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 2-bromo-4-methoxypyridine (1.21 g), 4-chlorophenylboronic acid (1.21 g) and tetrakis(triphenylphosphine)-palladium (372 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (7.74 ml). The mixture was stirred at 80° C. for 12 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. 2-Propanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-chlorobenzene (1.03 g).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. addition2-Propanol was added to the residue
  7. filtrationThe precipitate was collected by filtration
  8. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7b4452f4ded145f882779aa1ceb51230
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521643B1

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