Dimethylformamide → 1-(4-Methylphenyl)pyrene

HRID 1914395Notes

Reaction equation

HRID 1914395 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 and stirred under a nitrogen gas stream at 120° C. for 5 hours. The solution was cooled to room temperature and 1.6 L of water was poured into the solution, 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 resulting solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate and then filtered through Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of methanol, and then the precipitated solid was collected by filtration and vacuum-dried to obtain 40.0 g of 1-(4-methylphenyl)pyrene.

Workup

  1. temperatureThe solution was cooled 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 resulting solid was dissolved in 500 ml of dichloromethane
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered through Celite
  8. customThe filtrate was evaporated
  9. washthe residue was washed twice with 200 ml of methanol
  10. filtrationthe precipitated solid was collected by filtration
  11. customvacuum-dried

Sources & evidence

ORD record
ord-5d54889bbd79488698b07bff408c430e
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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