Ethyl bromoacetate → HCID 89768047, compound

HRID 591478Notes

Reaction equation

HRID 591478 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]([OH:18])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:8]=2[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C=O)C.O>[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH2:4][O:5][C:6]1[CH:20]=[CH:19][C:9]2[C:10]([O:18][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:12][C:8]=2[CH:7]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 89767819HCID 89767819, compound

Product 1

HCID 89768047HCID 89768047, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 6-((2,4-dichlorobenzyl)oxy)-3-hydroxy-1-benzothiophene-2-carboxylate (200 mg) in DMF (dry) (5.0 mL) were added K2CO3 (104 mg) and ethyl 2-bromoacetate (0.084 mL). The mixture was stirred at room temperature for 16 h. The mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed successively with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (152.7 mg).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layer was washed successively with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-1b75888dc3f44e41bf12dde4804e9cda
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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