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

HRID 1027322Notes

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

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 with stirring under a nitrogen gas flow at 40° C. for 7 hours. After cooling the solution to room temperature, 1.0 L of water was injected, followed by extraction with 500 ml of dichloromethane. The organic layer was washed twice with 200 ml of water, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of ethyl acetate. The precipitated solid was collected by filtration and then vacuum-dried to obtain 11.4 g of 1-bromo-6-(4-methylphenyl)pyrene.

Workup

temperatureAfter cooling the solution 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
customevaporated
filtrationfiltered
customThe filtrate was evaporated
washthe residue was washed twice with 200 ml of ethyl acetate
filtrationThe precipitated solid was collected by filtration
customvacuum-dried

Sources & evidence

ORD record: ord-2e652977696d429aaa7a082da987909a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729530B2

Reaction notes

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