Dimethylformamide → 1-(3,5-Dichlorophenyl)-6-(4-methylphenyl)pyrene

HRID 1914400Notes

Reaction equation

HRID 1914400 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]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([Cl:32])[CH:31]=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>[Cl:25][C:26]1[CH:27]=[C:28]([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:18]3[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:29]=[C:30]([Cl:32])[CH:31]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 27343313,5-Dichlorophenylboronic acidHCID 861013611-Bromo-6-(4-methylphenyl)pyrene

Product 1

HCID 861013811-(3,5-Dichlorophenyl)-6-(4-methylphenyl)pyreneYield 58.4%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

A mixed solution of 8.0 g of 1-bromo-6-(4-methylphenyl)pyrene, 4.5 g of 3,5-dichlorophenylboronic acid, 9.2 g of tripotassium phosphate, 1.4 g of tetrabutylammonium bromide, 97 mg of palladium acetate and 215 ml of dimethylformamide was heated and stirred under a nitrogen gas stream at 120° C. for 5 hours. The solution was cooled to room temperature and 1.0 L of water was poured into the solution, followed by extraction with 600 ml of dichloromethane. The organic layer was washed twice with 200 ml of water, dried over magnesium sulfate and then filtered through Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of ethyl acetate, and then the precipitated solid was collected by filtration. The precipitated solid was recrystallized from 100 ml of dimethylformamide and then vacuum-dried to obtain 5.5 g of 1-(3,5-dichlorophenyl)-6-(4-methylphenyl)pyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionfollowed by extraction with 600 ml of dichloromethane
  3. washThe organic layer was washed twice with 200 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through Celite
  6. customThe filtrate was evaporated
  7. washthe residue was washed twice with 200 ml of ethyl acetate
  8. filtrationthe precipitated solid was collected by filtration
  9. customThe precipitated solid was recrystallized from 100 ml of dimethylformamide
  10. customvacuum-dried

Sources & evidence

ORD record
ord-52661c09f5294f2fb52ef56def469bcd
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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