2-Chloroanthracene → 2-Phenylanthracene

HRID 2425801

Reaktionsgleichung

Reaktionsgleichung von HRID 2425801
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-704b3e31ffae423b90613d7e1090f63d
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07964293B2

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