Water → 3-(2-Hydroxyphenyl)pyridine

HRID 63374

Reaktionsgleichung

Reaktionsgleichung von HRID 63374
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=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]>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[OH:8])[CH:10]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 72442-BromophenolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acid

Produkt 1

HCID 125036743-(2-Hydroxyphenyl)pyridineAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

2-Bromophenol (0.5 g, 2.9 mmol) was dissolved in dimethoxyethane/water (2:1). Pyridin-3-ylboronic acid (0.71 g, 5.8 mmol) and Pd(dppf)Cl2 (0.12 g, 0.14 mmol), sodium carbonate (1.2 g, 14 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-(pyridin-3-yl)phenol (0.25 g, 20%).

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-95095235c5cc4695bc5b6653df5da0b5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447083B2

Verknüpfte Notizen

Wird geladen…