Ethyl bromoacetate → Methyl 4-chloro-2-(2-ethoxy-2-oxoethoxy)benzoate

HRID 1403371Notes

Reaction equation

HRID 1403371 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Product 1

HCID 70665052Methyl 4-chloro-2-(2-ethoxy-2-oxoethoxy)benzoateYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 4-chloro-2-hydroxybenzoate (21 g, 112.55 mmol) in acetone (200 mL) was added ethyl 2-bromoacetate (28.3 g, 169.46 mmol) and potassium carbonate (23.4 g, 169.31 mmol). After refluxing for 3 h, the solids were collected by filtration. The resulting mixture was concentrated under vacuum, dissolved in petroleum ether (300 mL) and filtered to give methyl 4-chloro-2-(2-ethoxy-2-oxoethoxy)benzoate as a red solid (26 g, 85%).

Workup

  1. temperatureAfter refluxing for 3 h
  2. filtrationthe solids were collected by filtration
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. dissolutiondissolved in petroleum ether (300 mL)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c6a4d87291704fe6bbf42c4cf3f5747d
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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