O-Cresol → HCID 67076683, Verbindung

HRID 521501

Reaktionsgleichung

Reaktionsgleichung von HRID 521501
C(=O)([O-])[O-].[K+].[K+].[C:7]1([CH3:14])[C:12]([OH:13])=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:19]([OH:21])=[O:20]>CN(C=O)C.[Cu]>[CH3:26][O:25][C:24]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][C:16]=1[O:13][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:14]

Komponenten

6

Edukt 3

HCID 335O-Cresol2×HCID 11430Potassium Carbonate2×HCID 668363-Bromo-4-methoxybenzoic acid

Produkt 1

HCID 67076683HCID 67076683, VerbindungAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

Potassium carbonate (1.20 g, 8.66 mmol), o-cresol (468 mg, 4.33 mmol), copper powder (28 mg, 0.43 mmol) and 3-bromo-4-methoxybenzoic acid (1.00 g, 4.33 mmol) were suspended in DMF (5 ml) and heated to 165° C. overnight. Potassium carbonate (1.20 g, 8.66 mmol) and o-cresol (468 mg, 4.33 mmol) were added once again and heating was continued for another 2 h. The crude mixture was partitioned between EA and 2 N hydrochloric acid, the aqueous phase extracted with EA, and the combined organic phases were dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified by silica gel chromatography (HEP/EA gradient) to yield 600 mg of the title compound.

Aufarbeitung

  1. temperatureheating
  2. customThe crude mixture was partitioned between EA and 2 N hydrochloric acid
  3. extractionthe aqueous phase extracted with EA
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica gel chromatography (HEP/EA gradient)

Quellen und Nachweise

ORD-Eintrag
ord-013c62593d8d4919bc487603c80ca7a4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328071B2

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