Sodium Carbonate → 2,4-Dimethyl-6-(2-thienyl)phenol

HRID 63381

Reaktionsgleichung

Reaktionsgleichung von HRID 63381
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)[C:3]=1[OH:10]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 27339602-Thiopheneboronic acid

Produkt 1

HCID 900022172,4-Dimethyl-6-(2-thienyl)phenolAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Bromo-4,6-dimethylphenol (500 mg, 2.49 mmol), 2-thiophenyl boronic acid (88 mg, 2.99 mmol), sodium carbonate (791 mg, 7.47 mmol) and Pd2(dppf)2Cl2 (406 mg, 0.49 mmol) were dissolved in dimethoxyethane/water 6 mL/3 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 2,4-dimethyl-6-(thiophene-2-yl)phenol (231 mg, 45%).

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-d42cca8043834a089eaabd02a21e9477
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

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