Iodine → 2-Iodo-3-(4-methoxyphenylsulfonyl)propionic acid

HRID 1421518Notes

Reaction equation

HRID 1421518 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[I:6]I.[Na].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>C(Cl)Cl.[Cl-].[Na+].O.O>[I:6][CH:2]([CH2:3][S:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=1)(=[O:19])=[O:18])[C:1]([OH:5])=[O:4]

Participants

8

Reactant 4

HCID 807IodineHCID 6581Acrylic AcidHCID 39522614-MethoxybenzenesulfinateHCID 5360545Sodium

Product 1

HCID 187798602-Iodo-3-(4-methoxyphenylsulfonyl)propionic acidYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Added water (0.85 grams, 0.85 ml) followed by the acrylic acid (3.42 grams, 3.25 ml), then I2 (12.04 grams, 47.41 mmol) to a slurry of sodium (4-methoxybenzenesulfinate (9.11 grams, 46.94 mmol) in methylene chloride (150 ml). Added more methylene chloride (100 ml) so slurry could stir. Stirred at room temperature for weekend. Washed reaction solution with 1N Na2S2O3 (aq) (3×150 ml) until organic layer was colorless. Washed organic layer with brine. Dried (MgSO4), filtered and concentrated in vacuo, to give 4.23 grams (25%) of crude 2-iodo-3-(4-methoxyphenylsulfonyl)propionic acid.

Workup

  1. stirringStirred at room temperature for weekend
  2. washWashed
  3. customreaction solution with 1N Na2S2O3 (aq) (3×150 ml) until organic layer
  4. dry with materialDried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9141f9971fd241459614999d04153373
Source dataset
uspto-grants-2000_06
Patent number
US06077864

Reaction notes

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