2,4-Dimethylaniline → Bis(2,4-dimethylphenyl)amine

HRID 1776074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776074
[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1Br.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.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]>[CH3:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:12]1[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]=1[CH3:10]

Komponenten

6

Edukt 3

HCID 72502,4-DimethylanilineHCID 68503Benzene, 1-bromo-2,4-dimethyl-HCID 23676156Sodium t-butoxide

Produkt 1

HCID 21989085Bis(2,4-dimethylphenyl)amineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2,4-dimethylaniline (6.05 g, 50 mmol), 2,4-dimethylbromobenzene (9.25 g, 50 mmol), Pd(dppf)Cl2 (0.88 g, 1.2 mmol), sodium tert-butoxide (KOBut) (9.6 g, 0.1 mmol) in toluene (120 mL) was degassed and heated at 100° C. overnight. The resulting mixture was worked up with dichloromethane/brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1. After removal of solvent, a liquid was obtained (9.45 g, in 84% yield).

Aufarbeitung

  1. customwas degassed
  2. dry with materialdried over Na2SO4
  3. custompurified by flash column
  4. customAfter removal of solvent
  5. customa liquid was obtained (9.45 g, in 84% yield)

Quellen und Nachweise

ORD-Eintrag
ord-3c75b1fb2f9f411fa806453f0af00bce
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09263681B2

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