Methyl iodide → 2,7-Dibromo-9,9-dimethylfluorene

HRID 71902

Reaktionsgleichung

Reaktionsgleichung von HRID 71902
[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[C:4]=2[CH:3]=1.[OH-].[K+].[CH3:18]I.C(O[CH2:24][CH3:25])(=O)C>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:24]([CH3:25])([CH3:18])[C:13]=2[CH:14]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 1400732,7-Dibromofluorene

Produkt 1

HCID 121238762,7-Dibromo-9,9-dimethylfluoreneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,7-dibromo-9H-fluorene (1.0 g, 3.1 mmol), KI (50 mg, 0.3 mmol) and KOH (750 mg, 13.3 mmol) in DMSO was added methyl iodide (0.42 mL, 6.8 mmol). The mixture was stirred at room temperature for 16 hours, then diluted with ethyl acetate (100 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product 2,7-Dibromo-9,9-dimethyl-9H-fluorene as a white solid (1.1 g, 100%).

Aufarbeitung

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-984bb8523b8d407a82b2ebe6e3b58a57
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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