Potassium Hydroxide → 3,6-dibromo-9-(2-(oxiran-2-yl)ethyl)-9H-carbazole

HRID 62188

Reaktionsgleichung

Reaktionsgleichung von HRID 62188
[OH-].[K+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.Br[CH2:19][CH2:20][CH:21]1[O:23][CH2:22]1>CN(C=O)C.CCOC(C)=O>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:19][CH2:20][CH:21]3[CH2:22][O:23]3)[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 1004142-(2-Bromoethyl)oxiraneHCID 2748743,6-Dibromocarbazole

Produkt 1

HCID 580971883,6-dibromo-9-(2-(oxiran-2-yl)ethyl)-9H-carbazoleAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Crushed KOH (0.0054 g, 0.0954 mmol, 1.2 equiv) was added to 3,6-dibromocarbazole (0.0258 g, 0.0795 mmol, 1 equiv.) in 0.5 mL DMF solution and the mixture was stirred for 30 min. 1-Bromo-3,4-epoxybutane (0.0300 g, 0.199 mmol) in 0.5 mL DMF solution was dropwise added into the mixture and it was stirred at room temperature for overnight. Reaction crude was diluted with 20 mL EtOAc and washed with water 5×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford 31.2 mg white solid as product, yield 97.9%.

Aufarbeitung

  1. stirringwas stirred at room temperature for overnight
  2. customReaction crude
  3. washwashed with water 5×10 mL
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ef761b98f37543ebbfe6dd2e97743156
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446042B2

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