Di-tert-butylchlorophosphine → 4-(Bis(3-methylphenyl)amino)benz[a]-anthracene

HRID 877287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 877287
ClP(C(C)(C)C)C(C)(C)C.Br[C:12]1[C:17]2=[CH:18][CH:19]=[C:20]3[C:29]([CH:28]=[C:27]4[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]4)=[CH:21]3)=[C:16]2[CH:15]=[CH:14][CH:13]=1.[CH3:30][C:31]1[CH:32]=[C:33]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH3:44])[CH:39]=2)[CH:34]=[CH:35][CH:36]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:44][C:40]1[CH:39]=[C:38]([N:37]([C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([CH3:30])[CH:32]=2)[C:12]2[C:17]3=[CH:18][CH:19]=[C:20]4[C:29]([CH:28]=[C:27]5[C:22]([CH:23]=[CH:24][CH:25]=[CH:26]5)=[CH:21]4)=[C:16]3[CH:15]=[CH:14][CH:13]=2)[CH:43]=[CH:42][CH:41]=1

Komponenten

8

Edukt 4

HCID 139566Di-tert-butylchlorophosphineHCID 182324Benz(a)anthracene, 4-bromo-HCID 7016139m,m'-DitolylamineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 594126574-(Bis(3-methylphenyl)amino)benz[a]-anthracene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

190 μl (1 mmol) of chloro-di-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.4 g (50 mmol) of 4-bromobenz[a]anthracene, 11.8 g (60 mmol) of bis(3-methylphenyl)amine and 7.7 g (80 mmol) of sodium tert-butoxide in 500 ml of toluene, and the mixture is subsequently heated under reflux for 5 h. After the mixture has been cooled to 60° C., 500 ml of water are added, the organic phase is separated off, filtered through silica gel, evaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol are then added. After cooling, the solid is filtered off with suction. Recrystallisation five times from dioxane (about 8 ml/g); sublimation (p=5×10−5 mbar, T=280° C.). Yield: 11.9 g (28 mmol), 56.1%, purity 99.9% (HPLC).

Aufarbeitung

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 5 h
  3. customthe organic phase is separated off
  4. filtrationfiltered through silica gel
  5. customevaporated virtually to dryness at 80° C. in vacuo, and 300 ml of ethanol
  6. additionare then added
  7. temperatureAfter cooling
  8. filtrationthe solid is filtered off with suction
  9. customRecrystallisation five times from dioxane (about 8 ml/g)
  10. customsublimation (p=5×10−5 mbar, T=280° C.)

Quellen und Nachweise

ORD-Eintrag
ord-b725f01181bc4dc6bc9acb588e93bfa7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08986852B2

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