Sodium Hydroxide → 9-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene

HRID 42384

Reaktionsgleichung

Reaktionsgleichung von HRID 42384
[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.[OH-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:30]=[CH:29][C:28]2[CH2:27][CH2:26][C:25]=2[CH:24]=1>CS(C)=O>[C:25]12[CH2:26][CH2:27][C:28]=1[CH:29]=[CH:30][C:23]([CH2:22][CH2:21][CH2:20][CH2:19][C:5]1([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:24]=[C:25]4[C:28](=[CH:29][CH:30]=3)[CH2:27][CH2:26]4)[C:4]3[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=3[C:11]3[C:6]1=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)=[CH:24]2

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 1400732,7-DibromofluoreneHCID 580284923-(4-Bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene

Produkt 1

HCID 580284989-(4-(bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl)butyl)-9-(4-(bicyclo[4.2.0]octa-1,3,5-trien-3-yl)butyl)-2,7-dibromo-9H-fluorene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To an oven-dried three-neck round-bottom flask under nitrogen, were added 25.97 g of 2,7-dibromofluorene, 32.06 g sodium hydroxide, 1.33 g KI, and 300 mL anhydrous DMSO. The 46 g 3-(4-bromobutyl)bicyclo[4.2.0]octa-1(6),2,4-triene 300 mL anhydrous DMSO was added via cannula. The reaction was heated to 80° C. After 4 hours, the reaction was quenched by the addition of DI water (10 mL). The excess salt was removed by filtration. 500 mL Ethyl acetate was added, and extracted with DI water (3×300 mL) and brine (3×300 mL). The combined organic layer was dried over anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration, and the solvent was removed by rotary evaporation. The product (43 g) was purified by flash chromatography using hexane. The structure was confirmed by NMR.

Aufarbeitung

  1. customthe reaction was quenched by the addition of DI water (10 mL)
  2. customThe excess salt was removed by filtration
  3. addition500 mL Ethyl acetate was added
  4. extractionextracted with DI water (3×300 mL) and brine (3×300 mL)
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. customMagnesium sulfate was removed by filtration
  7. customthe solvent was removed by rotary evaporation
  8. customThe product (43 g) was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-eef2893e491a4d5ab05d9efdcf8e0d14
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08535974B2

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