Water → 2,6-Dimethyl-4-(5-pyrimidinyl)phenol

HRID 63371

Reaktionsgleichung

Reaktionsgleichung von HRID 63371
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[N:11]1[CH:16]=[C:15](B(O)O)[CH:14]=[N: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]>[CH3:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:16]=[N:11][CH:12]=[N:13][CH:14]=2)[CH:3]=[C:4]([CH3:10])[C:5]=1[OH:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 2795193(Pyrimidin-5-yl)boronic acid

Produkt 1

HCID 683349172,6-Dimethyl-4-(5-pyrimidinyl)phenolAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

4-Bromo-2,6-dimethylphenol (0.5 g, 2.5 mmol) was dissolved in dimethoxyethane/water (2:1). pyrimidin-5-ylboronic acid (0.37 g, 2.8 mmol), Pd(dppf)Cl2 (0.02 g, 0.13 mmol) and sodium carbonate (0.79 g, 7.5 mmol) were added thereto, followed by reacting in microwave reactor at 120° C. for 15 minutes. 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 2,6-dimethyl-4-(pyrimidin-5-yl)phenol (0.1 g, 20%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-34c8f6cb4a13436397cfcea4147ae4c2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

Verknüpfte Notizen

Wird geladen…