2-Chloroanthracene → 2-Phenylanthracene

HRID 221178

Reaktionsgleichung

Reaktionsgleichung von HRID 221178
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(C)C=CC=CC=1>[C:16]1([C:2]2[CH:15]=[CH:14][C:13]3[C:4](=[CH:5][C:6]4[C:11]([CH:12]=3)=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH:3]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 283082-ChloroanthraceneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic Acid

Produkt 1

HCID 5197172-PhenylanthraceneAusbeute 83,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 75806TricyclohexylphosphineKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Into a flask, 5.00 g of 2-chloroanthracene, 4.3 g of phenylboronic acid, 538 mg of tris(dibenzylieneacetone)dipalladium(0), 494 mg of tricyclohexyl phosphine, 9.98 g of tripotassium phosphate, and 75 ml of toluene were put, and the solution was stirred at reflux temperature for 2 hours under argon atmosphere. After heating, 1.5 liter of toluene was added to the reaction liquid, the liquid was cooled to room temperature and then filtrated, and thus the filtrates were purified by silica gel column chromatography. The filtrates were concentrated in an evaporator, the concentrates were recrystallized in toluene, and thus 5.0 g of 2-phenylanthracene was obtained.

Aufarbeitung

  1. temperatureat reflux temperature for 2 hours under argon atmosphere
  2. temperatureAfter heating
  3. filtrationfiltrated
  4. customthus the filtrates were purified by silica gel column chromatography
  5. concentrationThe filtrates were concentrated in an evaporator
  6. customthe concentrates were recrystallized in toluene

Quellen und Nachweise

ORD-Eintrag
ord-7e977a05d39941088a05831005e7e0cd
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202633B2

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