Sulfamic Acid → 3-Iodo-4,5-dimethoxybenzoic acid

HRID 638930Notes

Reaction equation

HRID 638930 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[CH:5]=[O:6].S(=O)(=O)([OH:16])N.[O-]Cl=O.[Na+]>CC#N.O>[CH3:13][O:12][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([I:1])[C:9]=1[O:10][CH3:11])[C:5]([OH:16])=[O:6]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 27781133-Iodo-4,5-dimethoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 2304593-Iodo-4,5-dimethoxybenzoic acidYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-iodo-4,5-dimethoxybenzaldehyde (25.0 g, 85.6 mmol) in CH3CN (800 mL) at room temperature, was added a solution of sulfamic acid (10.65 g, 109 mmol) in H2O (135 mL). To this was added, dropwise, a solution of NaClO2 (12.65 g, 112 mmol) in H2O (135 mL) over 20 min period. After stirring for a further 30 min at room temperature, the solvent was removed in vacuo. The reaction was diluted with 1.0 M aqueous HCl (700 mL) and extracted with EtOAc (3×300 mL). The combined organic layers were washed with brine (600 mL), dried over Na2SO4 and concentrated in vacuo to give 3,4-dimethoxy-5-iodobenzoic acid (26 g). The product was used without further purification.

Workup

  1. additionTo this was added
  2. customthe solvent was removed in vacuo
  3. additionThe reaction was diluted with 1.0 M aqueous HCl (700 mL)
  4. extractionextracted with EtOAc (3×300 mL)
  5. washThe combined organic layers were washed with brine (600 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3854cc589feb4fe09d8948507f8c74bd
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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