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

HRID 600163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 600163
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[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[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[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[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:24]3[C:25]6[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=6)[C:21]([CH3:20])=[CH:22][CH:23]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[C:4]([C:2]3[C:15]4[C:16](=[CH:17][CH:12]=[CH:13][CH:14]=4)[C:5]([CH3:6])=[CH:4][CH:3]=3)[CH:3]=2)=[CH:23][CH:22]=1

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 27735114-Methyl-1-naphthaleneboronic acidHCID 30159691,3,6-Tribromopyrene

Produkt 1

HCID 866285941,3,6-Tri(4-methylnaphthalene-1-yl)pyreneAusbeute 133,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixed solution of 2 g of 1,3,6-tribromopyrene, 3.4 g of 4-methyl-1-naphthaleneboronic acid, 5.8 g of tripotassium phosphate, 0.88 g of tetrabutylammonium bromide, 61 mg of palladium acetate and 140 ml of deaerated dimethylformamide was heated while stirred under nitrogen gas stream at a temperature of 130° C. for 9 hours. After cooling the mixed solution to room temperature, 500 ml of water was injected thereinto to extract therefrom with 200 ml of dichloromethane. The organic layer was washed twice with 100 ml of water, dried by magnesium sulfate and thereafter concentrated by evaporation. The organic layer was purified by silica gel column chromatography and vacuum dried under a temperature of 70° C. to obtain 1.9 g of 1,3,6-tri(4-methylnaphthalene-1-yl)pyrene as milky-white powder.

Aufarbeitung

  1. temperatureAfter cooling the mixed solution to room temperature
  2. extractionto extract
  3. washThe organic layer was washed twice with 100 ml of water
  4. dry with materialdried by magnesium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe organic layer was purified by silica gel column chromatography and vacuum
  7. customdried under a temperature of 70° C.

Quellen und Nachweise

ORD-Eintrag
ord-b0cacb832abe410d8ec327820bf53b00
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07901794B2

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