(3,4-Dimethoxyphenyl)acetic acid → 2-(2-iodo-4,5-dimethoxyphenyl)acetic acid

HRID 1691794Notes

Reaction equation

HRID 1691794 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[I:15]Cl.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[I:15][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 24640Iodine chlorideHCID 23665763Sodium Bisulfite

Product 1

HCID 2847432-(2-iodo-4,5-dimethoxyphenyl)acetic acidYield 44.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,4-Dimethoxyphenylacetic acid (4.0 g, 20.4 mmol) was dissolved in 100 ml of glacial acetic acid. Iodine monochloride (1.35 eq, 1.38 ml) was added slowly and the mixture was allowed to stir at room temperature overnight. To the mixture was added 300 ml of a 10% aqueous solution of sodium bisulfite. The mixture was concentrated in vacuo to remove most of the acetic acid. The aqueous residue was extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with diethyl ether and the solid was then filtered and dried to give (2-iodo-4,5-dimethoxy-phenyl)-acetic acid (2.94 g, 44.8%) as an off-white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove most of the acetic acid
  3. extractionThe aqueous residue was extracted with EtOAc
  4. dry with materialThe organic extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether
  8. filtrationthe solid was then filtered
  9. customdried

Sources & evidence

ORD record
ord-0caac006402c4ee68668d7ce2785a80a
Source dataset
uspto-grants-2012_04
Patent number
US08153808B2

Reaction notes

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