Potassium Phosphate, Tribasic → 4-Benz[a]anthracen-4-ylbenzaldehyde

HRID 877298

Reaktionsgleichung

Reaktionsgleichung von HRID 877298
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24].Br[C:35]1[C:40]2=[CH:41][CH:42]=[C:43]3[C:52]([CH:51]=[C:50]4[C:45]([CH:46]=[CH:47][CH:48]=[CH:49]4)=[CH:44]3)=[C:39]2[CH:38]=[CH:37][CH:36]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCOCC1>[CH:38]1[C:39]2=[C:52]3[C:43](=[CH:42][CH:41]=[C:40]2[C:35]([C:28]2[CH:29]=[CH:30][C:25]([CH:23]=[O:24])=[CH:26][CH:27]=2)=[CH:36][CH:37]=1)[CH:44]=[C:45]1[C:50]([CH:49]=[CH:48][CH:47]=[CH:46]1)=[CH:51]3

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 80271Tri-o-tolylphosphineHCID 182324Benz(a)anthracene, 4-bromo-HCID 5910734-Formylphenylboronic Acid

Produkt 1

HCID 594126624-Benz[a]anthracen-4-ylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

14 g (7.9 mmol) of tri-o-tolylphosphine and then 300 mg (1.3 mmol) of palladium(II) acetate are added to a well-stirred suspension of 50 g (333 mmol) of 4-formylphenylboronic acid, 81 g (266 mmol) of 4-bromobenz[a]anthracene and 118 g (558 mmol) of tripotassium phosphate in a mixture of 500 ml of toluene, 500 ml of dioxane and 400 ml of water, and the mixture is subsequently heated under reflux for 16 h. After cooling, the precipitated solid is filtered off with suction, washed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol and finally dried. Yield: 49.7 g (149 mmol), 56%.

Aufarbeitung

  1. temperaturethe mixture is subsequently heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed three times with 50 ml of toluene, three times with 50 ml of ethanol:water (1:1, v:v), three times with 100 ml of ethanol
  6. customfinally dried

Quellen und Nachweise

ORD-Eintrag
ord-d5cc62a83187442482c67e56821c102a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08986852B2

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