4-Iodophenol → Methyl 2-(4-iodophenoxy)acetate

HRID 343568Notes

Reaction equation

HRID 343568 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:13][C:11](=[O:12])[CH2:10][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 6457537Methyl 2-(4-iodophenoxy)acetateYield 62%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 4-iodophenol (0.50 g, 2.27 mmol), methyl 2-bromoacetate (0.382 g, 2.50 mmol), and powdered potassium carbonate (0.314 g, 2.27 mmol) in dry acetone under argon was sealed and heated at 70° C. for 4 hr. The cooled mixture was filtered, and the filtrate was evaporated in vacuo. The residue was purified by chromatography (silica, 40 to 50% methylene chloride in cyclohexane) and the solvent was removed in vacuo to afford the titled intermediate as a white solid (0.41 g, 62%), mp 69°-70° C.

Workup

  1. customwas sealed
  2. filtrationThe cooled mixture was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by chromatography (silica, 40 to 50% methylene chloride in cyclohexane)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b73b013a9cba4ca0b02958c4539764c7
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

Loading…