Dimethyl Sulfoxide → 2,7-Dibromo-9,9-di-n-octylfluorene

HRID 645307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645307
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[Na+].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:34]S(C)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:34][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:27][CH3:33])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[CH:3]=1

Komponenten

8

Edukt 5

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Produkt 1

HCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,7-di bromo fluorene (25 g, 77 mmol), octylbromide (44.7 g, 0.596 mols), sodium hydroxide (37.5 g, 0.937 mols), and tetrabutyl ammonium bromide (0.5 g, 1.55 mmol) were dissolved in dimethyl sulfoxide (75 ml)-water (37.5 ml) mixed solvent. It was kept warm at 80° C. for 6 hours. After cooling, toluene (100 ml) and water (100 ml) were added, and the organic layer was partitioned. The organic layer is washed with water, 3% hydrochloric acid, and water, and then dehydrated with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the crude product was purified by silica-gel chromatography, and 2,7-dibromo-9,9-dioctylfluorene was obtained. (Amount: 26.85 g, yield: 79%)

Aufarbeitung

  1. additionmixed solvent
  2. temperatureAfter cooling
  3. customthe organic layer was partitioned
  4. washThe organic layer is washed with water, 3% hydrochloric acid, and water
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe crude product was purified by silica-gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aa7caae9fe6a44939a101baec01465c4
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07701129B2

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