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

HRID 405151

Reaktionsgleichung

Reaktionsgleichung von HRID 405151
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1B(O)O.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:9][C:3]1[CH:4]=[C:5]([NH2:6])[CH:7]=[CH:8][C:2]=1[C:14]1[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][C:15]=1[Cl:17]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 888884-Bromo-3-chloroanilineHCID 2734659(2,4-Dichlorophenyl)boronic acid

Produkt 1

HCID 866742502,2',4'-Trichloro-[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

4-Bromo-3-chloroaniline (3.0 g, 14.5 mmol), (2,4-dichlorophenyl)boronic acid (3.6 g, 18.9 mmol), Pd(dppf)Cl2 (1.2 g, 1.5 mmol), and K2CO3 (4.0 g, 29.1 mmol) were dissolved in 1,4-dioxane (60 mL) and water (15 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-a2084d23390e431ba692966ddb144432
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748624B2

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