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

HRID 638933Notes

Reaction equation

HRID 638933 reaction equation
[Br: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>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[C:5]([OH:16])=[O:6]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 28181443-bromo-4,5-dimethoxybenzoic acidYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-bromo-4,5-dimethoxybenzaldehyde (5.0 g, 20.5 mmol, 1 eq.) in CH3CN (192 mL) at room temperature was added a solution of sulfamic acid (2.55 g, 26.3 mmol) in H2O (32 mL) followed by a dropwise addition of a solution of NaClO2 (3.03 g, 26.8 mmol, 1.3 eq.) in H2O (32 mL) over 20 min period. After stirring for 30 min at room temperature, the solvent was removed in vacuo. The residue was dissolved in 1.0 M aqueous HCl (300 mL) and extracted with EtOAc (3×100 mL). The combined organic layer was washed with brine (300 mL), dried over Na2SO4 and concentrated in vacuo to give 3-bromo-4,5-dimethoxybenzoic acid (5.0 g). The product was used without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 1.0 M aqueous HCl (300 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organic layer was washed with brine (300 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c5c80e43bfc4efbbd05aed4ac2cf340
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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