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Diphenylamine → 5-(Diphenylamino)benzo[c]phenanthrene

HRID 2371240
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371240
ClP(C(C)(C)C)C(C)(C)C.Br[C:12]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:16]=[CH:15][C:14]=2[CH:13]=1.[C:30]1([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:37]1([N:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:12]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23]3[C:22]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[CH:16]=[CH:15][C:14]=3[CH:13]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 11487DiphenylamineHCID 139566Di-tert-butylchlorophosphineHCID 106624825-Bromobenzo[c]phenanthreneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 585113625-(Diphenylamino)benzo[c]phenanthrene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845
palladium(II) acetate
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

190 μl (1 mmol) of chlorodi-tert-butylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 15.3 g (50 mmol) of 5-bromobenzo[c]phenanthrene, 10.2 g (60 mmol) of diphenylamine 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. The product is purified by recrystallisation from dioxane five times (about 8 ml/g). Yield: 12.6 g (32 mmol), 64.1%, 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. customThe product is purified by recrystallisation from dioxane five times (about 8 ml/g)

Quellen und Nachweise

ORD-Eintrag
ord-1757804d8899434782ba850dd45ce2c7
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710284B2

Notizen zur Reaktion

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