2-Bromotoluene → Benzenamine, 2-methyl-N-(2-methylphenyl)-

HRID 1626240

Reaktionsgleichung

Reaktionsgleichung von HRID 1626240
C(P(C(C)(C)C)C1C=CC=C[C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].ClC1C=CC=CC=1C.[NH2-:38].[Li+].CC(C)([O-])C.[Na+]>C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[C:12]1([CH3:7])[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[NH:38][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29]

Komponenten

10

Edukt 5

HCID 72362-BromotolueneHCID 72382-ChlorotolueneHCID 24532Lithium amideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

The round bottom flask was heated then allow to cool to room temperature under argon. Add Pd2(dba)3 (1.39 g, 1.52 mmoles, 1.0 mol %) or Pd(dba)2 (1.38 g, 2.4 mmol, 1.4 mol %), 2-(di-tert-butylphosphino)biphenyl (1.09 g, 3.65 mmol, 2.4 mol %), 2-bromotoluene (40 mL, 332.1 mmoles) or 2-chlorotoluene (39 mL, 332.1 mmoles), lithium amide (3.47 g, 151.1 mmol, 45 mol %), sodium t-butoxide 29.5 g, 297.7 mmoles, 90 mol %), then toluene (150 mL). Heat at 80° C. under argon overnight. Let cool to room temperature. Diluted with diethyl ether then filtered through a pad of celite. Concentrated the resulting filtrate in vacuo. Used in the next reaction without purification. Purified the resulting residue by column chromatography with hexane to give the product as white crystals with a yellow tint (23.4 g, 118.6 mmol, 72% yield).

Aufarbeitung

  1. temperatureThe round bottom flask was heated
  2. temperatureHeat at 80° C. under argon overnight
  3. temperatureLet cool to room temperature
  4. filtrationthen filtered through a pad of celite
  5. concentrationConcentrated the resulting filtrate in vacuo
  6. customUsed in the next reaction
  7. customwithout purification
  8. customPurified the resulting residue by column chromatography with hexane

Quellen und Nachweise

ORD-Eintrag
ord-bc28434e357143fbb628c77639ce971c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785434B2

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