Ethyl bromoacetate → Ethyl 2-(3,6-dibromo-9H-carbazol-9-yl)acetate

HRID 508235Notes

Reaction equation

HRID 508235 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[OH-].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O.C(OCC)(=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 14385110Ethyl 2-(3,6-dibromo-9H-carbazol-9-yl)acetateYield 96.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,6-dibromocarbazole (325.0 mg, 1.0 mmol, 1 equiv) in anhydrous N,N-dimethylformamide (5 mL) was added crushed KOH (67.3 mg, 1.2 mmol, 1.2 equiv). The mixture was stirred for 30 minutes. Ethyl bromoacetate (277.2 μL, 2.5 mmol, 2.5 equiv) was added into the mixture and it was stirred at room temperature overnight. The reaction crude was diluted with ethyl acetate (30 mL) and washed with 1M HCl and water. The organic layer was dried with MgSO4 and the concentrated to afford 396.3 mg white solid as product (96.4%).

Workup

  1. stirringwas stirred at room temperature overnight
  2. customThe reaction crude
  3. washwashed with 1M HCl and water
  4. dry with materialThe organic layer was dried with MgSO4
  5. concentrationthe concentrated

Sources & evidence

ORD record
ord-5a24654fad78476b8a72c03057ef1813
Source dataset
uspto-grants-2015_08
Patent number
US09095572B2

Reaction notes

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