Dimethylformamide → 3-Bromo-1,6-bis(4-methylphenyl)pyrene

HRID 600166Notes

Reaction equation

HRID 600166 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][C:15]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:14]5[CH:13]=[CH:12][C:11]4=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:31]N1C(=O)CCC1=O.CN(C)C=O>O>[Br:31][C:17]1[CH:16]=[C:15]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)[C:14]2[C:23]3=[C:22]4[C:11]([CH:10]=[CH:9][C:8]([C:5]5[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=5)=[C:21]4[CH:20]=[CH:19][C:18]=13)=[CH:12][CH:13]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 207305171,6-Bis(4-methylphenyl)pyrene

Product 1

HCID 866285953-Bromo-1,6-bis(4-methylphenyl)pyreneYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, a mixed solution of 1.3 g of 1,6-bis(4-methylphenyl)pyrene, 0.6 g of N-bromosuccinimide and 30 ml of dimethylformamide was stirred under nitrogen gas stream at a temperature of 60° C. for 5 hours. After cooling the mixed solution to room temperature, 30 ml of water was injected thereinto to extract therefrom with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried by magnesium sulfate and thereafter evaporated. The organic layer was recrystallized from toluene and vacuum dried to thereafter obtain 0.7 g of 3-bromo-1,6-bis(4-methylphenyl)pyrene.

Workup

  1. extractionto extract
  2. washThe organic layer was washed twice with 50 ml of water
  3. dry with materialdried by magnesium sulfate
  4. customevaporated
  5. customThe organic layer was recrystallized from toluene and vacuum
  6. customdried

Sources & evidence

ORD record
ord-0a4f29189bd14aec885d8427fa1c2860
Source dataset
uspto-grants-2011_03
Patent number
US07901794B2

Reaction notes

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