Dimethylformamide → 1-Bromo-6-(4-methylphenyl)pyrene

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Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]3[C:22]4=[C:23]5[C:18](=[CH:19][CH:20]=3)[CH:17]=[CH:16][CH:15]=[C:14]5[CH:13]=[CH:12][C:11]4=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:24][C:15]1[C:14]2[C:23]3=[C:22]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)=[C:21]4[CH:20]=[CH:19][C:18]3=[CH:17][CH:16]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

Next, a mixed solution of 40.0 g of 1-(4-methylphenyl)pyrene, 24.4 g of N-bromosuccinimide and 1.4 L of dimethylformamide was heated and stirred under a nitrogen gas stream at 40° C. for 7 hours. The solution was cooled to room temperature and 1.0 L of water was poured into the solution, followed by extraction with 500 ml of dichloromethane. The organic layer was washed twice with 200 ml of water, dried over magnesium sulfate and then filtered through Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of ethyl acetate, and then the precipitated solid was collected by filtration and vacuum-dried to obtain 11.4 g of 1-bromo-6-(4-methylphenyl)pyrene.

Aufarbeitung

temperatureThe solution was cooled to room temperature
extractionfollowed by extraction with 500 ml of dichloromethane
washThe organic layer was washed twice with 200 ml of water
dry with materialdried over magnesium sulfate
filtrationfiltered through Celite
customThe filtrate was evaporated
washthe residue was washed twice with 200 ml of ethyl acetate
filtrationthe precipitated solid was collected by filtration
customvacuum-dried

Quellen und Nachweise

ORD-Eintrag: ord-e9f018d29e034c41b32306ccaaea1c16
Quelldatensatz: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08610345B2

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