Dimethylformamide → 1-(4-Methylphenyl)pyrene

HRID 1670053Notes

Reaction equation

HRID 1670053 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 g of 1-bromopyrene, 21.7 g of 4-methylphenylboronic acid, 34 g of tribasic potassium phosphate, 10.3 g of tetrabutylammonium bromide, 0.71 g of palladium acetate, and 1.6 l (liters) of dimethylformamide was heated and stirred at 120° C. for 5 hours under a nitrogen stream. After the mixture was cooled to room temperature, 1.6 l of water was added thereto and stirred at room temperature for 0.5 hours. The precipitated solid was separated by filtration and washed twice with 200 ml of water. The resulting solid was dissolved in 500 ml of dichloromethane. The solution was dried over magnesium sulfate and then filtered through celite. The filtrate was evaporated, and the resulting residue was washed twice with 200 ml of methanol. The precipitated solid was separated by filtration and dried under vacuum to give 40 g of 1-(4-methylphenyl)pyrene.

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. stirringstirred at room temperature for 0.5 hours
  3. customThe precipitated solid was separated by filtration
  4. washwashed twice with 200 ml of water
  5. dissolutionThe resulting solid was dissolved in 500 ml of dichloromethane
  6. dry with materialThe solution was dried over magnesium sulfate
  7. filtrationfiltered through celite
  8. customThe filtrate was evaporated
  9. washthe resulting residue was washed twice with 200 ml of methanol
  10. customThe precipitated solid was separated by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-f2cdb81069c4492a8dc54730d0ec25fc
Source dataset
uspto-grants-2011_08
Patent number
US07989802B2

Reaction notes

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