Dimethylformamide → 1,6-Bis(4-methylphenyl)pyrene

HRID 1027315Notes

Reaction equation

HRID 1027315 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C)C=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:2]3[CH:15]=[CH:16][C:5]([CH3:6])=[CH:4][CH:3]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 176470Pyrene, 1,6-Dibromo-

Product 1

HCID 207305171,6-Bis(4-methylphenyl)pyreneYield 122.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixed solution of 2 g of 1,6-dibromopyrene, 1.9 g of 4-methylphenylboronic acid, 5.9 g of tripotassium phosphate, 0.9 g of tetrabutylammonium bromide, 15 mg of palladium acetate and 30 ml of dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 6 hours. After cooling the solution to room temperature, 30 ml of water was injected, followed by filtration. The resultant solid was washed with 30 ml of ethanol, recrystallized from toluene and then vacuum-dried to obtain 1.3 g of 1,6-bis(4-methylphenyl)pyrene.

Workup

  1. temperatureAfter cooling the solution to room temperature
  2. filtrationfollowed by filtration
  3. washThe resultant solid was washed with 30 ml of ethanol
  4. customrecrystallized from toluene
  5. customvacuum-dried

Sources & evidence

ORD record
ord-9605f540a4104ca9a0d04d0f9bd30dc6
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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