Dimethylformamide → 1,6-Bis(4-methylphenyl)pyrene

HRID 600165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600165
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:2]3[CH:15]=[CH:16][C:5]([CH3:6])=[CH:4][CH:3]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 176470Pyrene, 1,6-Dibromo-

Produkt 1

HCID 207305171,6-Bis(4-methylphenyl)pyreneAusbeute 122,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixed solution of 2 g of 1,6-dibromopyrene, 1.9 g of 4-methylphenylboronic acid, 5.9 g of tripotassium phosphate, 0.9 g of tetrabutylammonium bromide, 15 mg of palladium acetate and 30 ml of dimethylformamide was heated while stirred under nitrogen gas stream at a temperature of 130° C. for 6 hours. After cooling the mixed solution to room temperature, 30 ml of water was injected thereinto and the resulting solution was filtered. The solid filtered off was washed with 30 ml of ethanol, and thereafter recrystallized from toluene and vacuum dried to thereafter obtain 1.3 g of 1,6-bis(4-methylphenyl)pyrene.

Aufarbeitung

  1. temperatureAfter cooling the mixed solution to room temperature
  2. filtrationthe resulting solution was filtered
  3. filtrationThe solid filtered off
  4. washwas washed with 30 ml of ethanol
  5. customrecrystallized from toluene and vacuum
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-39c8ea5691714e31a9bac6a09add5e5a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07901794B2

Notizen zur Reaktion

Wird geladen…