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

HRID 1670054Notes

Reaction equation

[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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixed solution of 40 g of 1-(4-methylphenyl)pyrene, 24.4 g of N-bromosuccinimide and 1.4 l of dimethylformamide was then heated and stirred at 40° C. for 7 hours under a nitrogen stream. After the mixture was cooled to room temperature, 1 l (liter) of water was added thereto, and the mixture was extracted 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 resulting residue was washed twice with 200 ml of ethyl acetate. The precipitated solid was separated by filtration and dried under vacuum to give 11.4 g of 1-bromo-6-(4-methylphenyl)pyrene.

Workup

temperatureAfter the mixture was cooled to room temperature
extractionthe mixture was extracted 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 resulting residue was washed twice with 200 ml of ethyl acetate
customThe precipitated solid was separated by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-d69012f647b04043bcfb39a3af3c3f44
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989802B2

Reaction notes

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