Dimethylformamide → 1-(4-Methylphenyl)pyrene

HRID 1027321Notes

Reaction equation

HRID 1027321 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][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([C:9]2[C:8]3[C:17]4=[C:16]5[C:5](=[CH:6][CH:7]=3)[CH:4]=[CH:3][CH:2]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 1596271-Bromopyrene

Product 1

HCID 578364111-(4-Methylphenyl)pyreneYield 85.7%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
120 °C

Procedure

A mixed solution of 45.0 g of 1-bromopyrene, 21.7 g of 4-methylphenylboronic acid, 34.0 g of tripotassium phosphate, 10.3 g of tetrabutylammonium bromide, 0.71 g of palladium acetate and 1.6 L of dimethylformamide was heated with stirring under a nitrogen gas flow at 120° C. for 5 hours. After cooling to room temperature, 1.6 L of water was injected, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 200 ml of water. The resultant solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate, evaporated and then filtered using Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of methanol. The precipitated solid was collected by filtration and then vacuum-dried to obtain 40.0 g of 1-(4-methylphenyl)pyrene.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringby stirring at room temperature for 0.5 hours
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed twice with 200 ml of water
  5. dissolutionThe resultant solid was dissolved in 500 ml of dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. washthe residue was washed twice with 200 ml of methanol
  11. filtrationThe precipitated solid was collected by filtration
  12. customvacuum-dried

Sources & evidence

ORD record
ord-6bbe71f8d6044014b8ed61b3f0e18ccc
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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