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Sodium Carbonate → 2-(4-Diethylcarbamoylphenyl)anisole

HRID 895619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 895619
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1OB(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1(C)C=CC=CC=1.O.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>[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH3:15])=[CH:8][CH:7]=1)=[O:5])[CH3:2]
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Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 875218N,N-diethyl-4-iodobenzamideHCID 21940032(2-Methoxyphenyl)boric acid

Produkt 1

HCID 223807362-(4-Diethylcarbamoylphenyl)anisoleAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel2×
HCID 1140TolueneLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

4-Diethylcarbamoyl-1-iodobenzene (100 mg) was dissolved in dimethoxyethane (1 ml), added with tetrakis(triphenylphosphine)palladium (19.1 mg) under argon atmosphere, and stirred at room temperature for 10 minutes. The reaction mixture was added with the solution of (2-methoxyphenyl)boric acid (100 mg) dissolved in toluene (0.5 ml) prepared above and a solution of sodium carbonate (105 mg) dissolved in water (0.5 ml) and stirred at 90° C. for 5.5 hours. The reaction mixture was added with water (2 ml) and extracted twice with dichloromethane (4 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1) to obtain 81.9 mg of the title compound. Yield: 88%.

Aufarbeitung

  1. stirringstirred at 90° C. for 5.5 hours
  2. extractionextracted twice with dichloromethane (4 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-8b08b9782b2c4ddf9b3feaf5b6da48e7
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06916822B2

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