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

HRID 1027319Notes

Reaction equation

HRID 1027319 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=[C:4](Br)[CH:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=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>[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([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=[C:4]([C:11]3[CH:10]=[CH:9][C:8]([CH3:7])=[CH:17][CH:12]=3)[CH:3]=2)=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 79799Tolylboronic acidHCID 30159691,3,6-Tribromopyrene

Product 1

HCID 866285911,3,6-Tri(4-methylphenyl)pyreneYield 167.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
130 °C

Procedure

Next, a mixed solution of 2.0 g of 1,3,6-tribromopyrene, 2.5 g of 4-methylphenylboronic acid, 5.8 g of tripotassium phosphate, 0.88 g of tetrabutylammonium bromide, 61 mg of palladium acetate and 137 ml of deaerated dimethylformamide was heated with stirring under a nitrogen gas flow at 130° C. for 9 hours. After cooling to room temperature, 800 ml of water was injected, followed by extraction with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried over magnesium sulfate and then evaporated. The resultant concentrate was purified by silica gel column chromatography and then vacuum-dried to obtain 1.8 g of 1,3,6-tri(4-methylphenyl)pyrene as a pale yellow powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by extraction with 200 ml of dichloromethane
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. concentrationThe resultant concentrate
  7. customwas purified by silica gel column chromatography
  8. customvacuum-dried

Sources & evidence

ORD record
ord-e068d6f8c028407fb4c7585fa03d15f9
Source dataset
uspto-grants-2014_05
Patent number
US08729530B2

Reaction notes

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