Water → 4'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine

HRID 405228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405228
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[C:12]([CH3:19])[CH:11]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.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]>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)=[C:12]([CH3:19])[CH:11]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 108934-IodoanilineHCID 11430Potassium CarbonateHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

Produkt 1

HCID 672116234'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-iodoaniline (3.3 g, 15.0 mmol), (4-chloro-2-methylphenyl)boronic acid (3.3 g, 19.5 mmol), Pd(dppf)Cl2 (1.22 g, 1.5 mmol), and K2CO3 (4.1 g, 30 mmol) were dissolved in 1,4-dioxane (60 mL) and water (15 mL) and heated to 90° C. After 3 h the resulting mixture was diluted EtOAc and water and the layers were separated. The organic layer was dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Aufarbeitung

  1. customEtOAc and water and the layers were separated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-68b862a9b07748e7a3e2226d2b47a193
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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