Ethyl bromoacetate → HCID 14303535, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[CH:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:17]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:7]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]2[CH:17]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:9][C:8]1=[O:10])[CH3:26]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of 42.8 mmol of 5-chloro-2,3-dihydro-2-oxo-3-phenylbenzofuran in 50 ml of anhydrous dimethylformamide is added at room temperature to a suspension of 42.8 mmol of sodium hydride in 20 ml of anhydrous dimethylformamide. The mixture is stirred for one hour at 20° C. and 42.8 mmol of ethyl bromoacetate are added. The mixture is stirred for 12 hours at 20° C., the medium concentrated under vacuum, the residue taken up in 200 ml of 1% strength hydrochloric acid solution, the aqueous phase extracted with benzene, the organic phase dried over anhydrous sodium sulfate, the solvent evaporated off and the crystalline residue washed with a solution of ethyl ether and acetone (90:10). After filtration, 25.8 mmol of crystals are collected.
Workup
- stirringThe mixture is stirred for 12 hours at 20° C.
- concentrationthe medium concentrated under vacuum
- extractionthe aqueous phase extracted with benzene
- dry with materialthe organic phase dried over anhydrous sodium sulfate
- customthe solvent evaporated off
- washthe crystalline residue washed with a solution of ethyl ether and acetone (90:10)
- customare collected
Sources & evidence
- ORD record
- ord-b492761ff00c4b2c8b476e1201508d11
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859700
Reaction notes
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