Ethyl bromoacetate → Acetic acid, (2-iodophenoxy)-, ethyl ester

HRID 1242276Notes

Reaction equation

HRID 1242276 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[I:1])[CH3:21]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 107842-IodophenolHCID 10796Cesium carbonate

Product 1

HCID 11808921Acetic acid, (2-iodophenoxy)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9.10 g (41.4 mmol) of o-iodophenol was dissolved in 102 ml of acetone and treated subsequently at 0° C. with 14.8 g (1.1 eq.) of cesium carbonate and 4.57 ml (1.0 eq.) of ethyl bromoacetate. After vigorous stirring for 1 h at ambient temperature and filtration, the bulk of solvent was evaporated and the residue redissolved in AcOEt. Washing with water, drying over magnesium sulfate, and evaporation of the solvents finally produced 12.66 g of pure title compound as colorless oil.

Workup

  1. filtrationfiltration
  2. customthe bulk of solvent was evaporated
  3. dissolutionthe residue redissolved in AcOEt
  4. washWashing with water
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents finally produced 12.66 g of pure title compound as colorless oil

Sources & evidence

ORD record
ord-ed5ddf3e21ca428ab866784a0aceb311
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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