Water → 4-(3-Furanyl)-2,6-dimethylphenol

HRID 63373

Reaktionsgleichung

Reaktionsgleichung von HRID 63373
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=2)=[CH:12]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 2734358Furan-3-boronic acid

Produkt 1

HCID 900025234-(3-Furanyl)-2,6-dimethylphenolAusbeute 68,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-Bromo-2,6-dimethylphenol (350 mg, 1.74 mmol), 3-furanylboronic acid (269 mg, 2.26 mmol), Pd(dppf)Cl2 (71 mg, 0.087 mmol) and sodium carbonate (553 mg, 5.22 mmol) were dissolved in DME:water=4 mL:2 mL, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The obtained filtrate was extracted with ethyl acetate, dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 4-(furan-3-yl)-2,6-dimethylphenol (225 mg, 50%).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. extractionThe obtained filtrate was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. custompurified by column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-2de7987e35f7458f8887fa5fbfa415af
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

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