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

HRID 1911586Notes

Reaction equation

HRID 1911586 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 580971883,6-dibromo-9-(2-(oxiran-2-yl)ethyl)-9H-carbazoleYield 99.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-b33319fab6c34e4586e6c57b84140bb8
Source dataset
uspto-grants-2013_12
Patent number
US08604074B2

Reaction notes

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