Water → Methyl 2-(3-iodophenoxy)acetate

HRID 1352844Notes

Reaction equation

HRID 1352844 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][C:11]([O:13][CH2:14]C)=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 122723-Iodophenol

Product 1

HCID 13827037Methyl 2-(3-iodophenoxy)acetateYield 99.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Iodophenol (4.00 g, 18.2 mmol), ethyl bromoacetate (2.98 g, 18.2 mmol) and potassium carbonate (2.51 g, 18.2 mmol) were refluxed in acetone (40 ml) for 2 hours. The reaction mixtute was poured into water and extracted with ethyl acetate. The organic layer was dried, and filtered. The filtrate was concentrated and the residue was purified with silica gel chromatography to give the subject compound (5.30 g, 99%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-1c475b3ce78f40a596efadb019f535d1
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

Loading…