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

HRID 600165Notes

Reaction equation

HRID 600165 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 while stirred under nitrogen gas stream at a temperature of 130° C. for 6 hours. After cooling the mixed solution to room temperature, 30 ml of water was injected thereinto and the resulting solution was filtered. The solid filtered off was washed with 30 ml of ethanol, and thereafter recrystallized from toluene and vacuum dried to thereafter obtain 1.3 g of 1,6-bis(4-methylphenyl)pyrene.

Workup

  1. temperatureAfter cooling the mixed solution to room temperature
  2. filtrationthe resulting solution was filtered
  3. filtrationThe solid filtered off
  4. washwas washed with 30 ml of ethanol
  5. customrecrystallized from toluene and vacuum
  6. customdried

Sources & evidence

ORD record
ord-39c8ea5691714e31a9bac6a09add5e5a
Source dataset
uspto-grants-2011_03
Patent number
US07901794B2

Reaction notes

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