Sodium Carbonate → 2-(3-Furanyl)-6-methylphenol

HRID 63377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63377
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[O:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[O:10]1[CH:14]=[CH:13][C:12]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=2[OH:9])=[CH:11]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 110953292-Bromo-6-methylphenol

Produkt 1

HCID 121871312-(3-Furanyl)-6-methylphenolAusbeute 36,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Bromo-6-methylphenol (800 mg, 4.28 mmol), 3-furan boronic acid (574 mg, 5.13 mmol), sodium carbonate (1400 mg, 12.8 mmol) and Pd2(dppf)2Cl2 (699 mg, 0.82 mmol) were dissolved in dimethoxyethane/water 10 mL/10 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 filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (ethyl acetate:hexane=1:3) to obtain 2-(furan-3-yl)-6-methylphenol (273 mg, 26%).

Aufarbeitung

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was added with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over magnesium sulfate
  6. custompurified by column chromatography (ethyl acetate:hexane=1:3)

Quellen und Nachweise

ORD-Eintrag
ord-55e799f7c5b64012aa686c6ce8a522b7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

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