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

HRID 1914418Notes

Reaction equation

HRID 1914418 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 4 g of 1,6-dibromopyrene, 3.8 g of 4-methylphenylboronic acid, 12 g of tripotassium phosphate, 2 g of tetrabutylammonium bromide, 30 mg of palladium acetate and 60 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 130° C. for 6 hours. The solution was cooled to room temperature and 60 ml of water was poured into the solution, followed by filtration. The resulting solid was washed with 60 ml of ethanol, recrystallized from toluene and then vacuum-dried to obtain 2.6 g of 1,6-bis(4-methylphenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. washThe resulting solid was washed with 60 ml of ethanol
  4. customrecrystallized from toluene
  5. customvacuum-dried

Sources & evidence

ORD record
ord-8985ff197a6746f0bdd959582ed7626f
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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