Sodium Carbonate → 2-Phenylanthracene

HRID 68515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 68515
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:24]=[CH:23][C:22]2[C:13](=[CH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18](Br)=[CH:17][CH:16]=3)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]1([C:18]2[CH:17]=[CH:16][C:15]3[C:20](=[CH:21][C:22]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:24][CH:23]=4)[CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 220589062,6-Dibromoanthracene

Produkt 1

HCID 5197172-PhenylanthraceneAusbeute 128,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, 29.0 g of phenylboronic acid, 25.7 g of 2,6-dibromoanthracene, 4.62 g of tetrakis(triphenyl phosphine) palladium (0), 800 mL of toluene, and 400 mL of a 2-M aqueous solution of sodium carbonate were loaded, and then the mixture was stirred for 8 hours under reflux. After the mixture had been cooled to room temperature, the precipitated crystal was taken by filtration. The resultant solid was repeatedly recrystallized with toluene and hexane and washed. Thus, 25.0 g of 2-phenylanthracene were obtained (in 75% yield).

Aufarbeitung

  1. temperatureunder reflux
  2. filtrationthe precipitated crystal was taken by filtration
  3. customThe resultant solid was repeatedly recrystallized with toluene and hexane
  4. washwashed

Quellen und Nachweise

ORD-Eintrag
ord-f56fdcfdc2804a3b80d5a9f25e601eb5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822041B2

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