Iodine chloride → HCID 67245448, compound

HRID 2425584Notes

Reaction equation

HRID 2425584 reaction equation
[CH3:1][C:2]([CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH3:16])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[I:18]Cl>C(O)(=O)C.O>[CH3:17][C:2]([CH3:1])([C:8]1[CH:13]=[CH:12][C:11]([I:18])=[C:10]([O:14][CH2:15][CH3:16])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 67245940HCID 67245940, compound

Product 1

HCID 67245448HCID 67245448, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

To a cooled solution (5° C.) of ethyl dimethyl-3-ethoxyphenylacetate (5.0 g, 21.1 mmol) in acetic acid (40 mL) was added dropwise a solution of iodine monochloride (5.0 g, 30.9 mmol) in acetic acid. The reaction was stirred at room temperature for 18 h and diluted with water and extracted with methylene chloride. The combined organic layers were washed with aqueous sodium thiosulfate, aqueous sodium bicarbonate and brine. The solution was dried over anhydrous magnesium sulfate, filtered and concentrated to give ethyl dimethyl-(3-ethoxy-4-iodophenyl)acetate (6.25 g, 82%) as a yellow oil.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic layers were washed with aqueous sodium thiosulfate, aqueous sodium bicarbonate and brine
  3. dry with materialThe solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-72acd4dda32f4e2b9544cb12a3ef551f
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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