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

HRID 2167125

Reaktionsgleichung

Reaktionsgleichung von HRID 2167125
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1I)[NH2:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([CH3:20])[CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=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]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:5])[CH:6]=[CH:7][C:8]=1[C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][C:13]=1[CH3:20]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2829263-Chloro-4-iodoanilineHCID 5017600(4-Chloro-2-methylphenyl)boronic acid

Produkt 1

HCID 866742052,4'-Dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-Chloro-4-iodoaniline (3.0 g, 11.8 mmol), (4-chloro-2-methylphenyl)boronic acid (2.4 g, 14.2 mmol), Pd(dppf)Cl2 (1.0 g, 1.2 mmol), and K2CO3 (3.3 g, 23.7 mmol) were dissolved in 1,4-dioxane (40 mL) and water (10 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Quellen und Nachweise

ORD-Eintrag
ord-b8a4e7c28d2a4390a2492c80ad4c8f0a
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045389B2

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