Ethyl bromoacetate → HCID 11808055, compound
Reaction equation
[OH:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:14])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[N+:11]([C:10]1[C:2]([O:1][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:3][CH:4]=[C:5]2[C:9]=1[C:8](=[O:14])[CH2:7][CH2:6]2)([O-:13])=[O:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 6-hydroxy-7-nitro-1indanone (8.0 g, 41 mmol.) in N,N-dimethylformamide (50 mL) was added potassium carbonate (11.7 g, 82 mmol.). The mixture was stirred under ice-cooling, to which was added dropwise ethyl bromoacetate (5.5 mL, 50 mmol.). The reaction mixture was then stirred for one hour at room temperature, which was poured into ice-water, followed by extracting the organic matter with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting crystalline precipitate was collected by filtration and washed with hexane to afford the title compound (yield 10.8 g, 94%).
Workup
- temperaturecooling, to which
- stirringThe reaction mixture was then stirred for one hour at room temperature
- extractionby extracting the organic matter with ethyl acetate
- washThe extract solution was washed with a saturated aqueous saline solution and water, which
- dry with materialwas then dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- filtrationThe resulting crystalline precipitate was collected by filtration
- washwashed with hexane
Sources & evidence
- ORD record
- ord-11ada260b5594d47ba2b30d6ffeade79
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218429B1
Reaction notes
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