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

HRID 1027316Notes

Reaction equation

HRID 1027316 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 64.3%

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 a nitrogen gas flow at 60° C. for 5 hours. After cooling the solution to room temperature, 30 ml of water was injected, followed by extraction with 100 ml of dichloromethane. The organic layer was washed twice with 50 ml of water, dried over magnesium sulfate and then evaporated. The resultant solid was recrystallized from toluene and then vacuum-dried to obtain 1.0 g of 3-bromo-1,6-bis(4-methylphenyl)pyrene.

Workup

  1. extractionfollowed by extraction with 100 ml of dichloromethane
  2. washThe organic layer was washed twice with 50 ml of water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe resultant solid was recrystallized from toluene
  6. customvacuum-dried

Sources & evidence

ORD record
ord-12b2abdae74b4718a7efbb81c4d1bb41
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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