Water → 2,4-Dimethyl-6-(4-pyridinyl)phenol

HRID 63376

Reaktionsgleichung

Reaktionsgleichung von HRID 63376
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[N:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.O.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]>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)[C:3]=1[OH:10]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 2734379(Pyridin-4-yl)boronic acid

Produkt 1

HCID 1364905592,4-Dimethyl-6-(4-pyridinyl)phenolAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 18180031Water 1,2-dimethoxyethaneLösungsmittel

Versuchsvorschrift

2-Bromo-4,6-dimethylphenol (0.5 g, 2.5 mmol) was dissolved in dimethoxyethane/water (2:1). Pyridin-4-ylboronic acid (0.32 g, 2.5 mmol) and Pd(dppf)Cl2 (0.10 g, 0.13 mmol), sodium carbonate (1 g, 13 mmol) were added thereto, followed by stirring for 1 hour under reflux. After the completion of the reaction, the reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 2,4-dimethyl-6-(pyridin-4-yl)phenol (0.15 g, 30%).

Aufarbeitung

  1. temperatureunder reflux
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-64de13d8a55b40b4a50f41a2d31d6cb7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

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