2-Iodoxybenzoic acid → HCID 178519426, compound

HRID 1266036Notes

Reaction equation

HRID 1266036 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][OH:13])=[CH:8][CH:7]=2)[N:3]=[CH:2]1.I(C1C=CC=CC=1C(O)=O)(=O)=O>CS(C)=O>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:7]=[CH:8][C:9]([CH:12]=[O:13])=[CH:10][CH:11]=2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 178519427HCID 178519427, compound

Product 1

HCID 178519426HCID 178519426, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[4-(1H-Imidazol-4-yl]-phenyl]-methanol (0.21 g, 1.23 mmol) was dissolved in DMSO (12 mL). o-Iodoxybenzoic acid (Frigerio, et al., J. Org. Chem. 1995, 60, 7272) (1.03 g, 3.70 mmol) was added, and the reaction stirred at room temperature for 3.5 hours. The solvent was removed in vacuo, and the residue dissolved in 4:1 CHCl3/iPrOH. The resultant solids were filtered off, and the filtrate washed in turn with 5% Na2SO3/5% NaHCO3 solution, water, and brine, dried (MgSO4) and the solvent removed to give 0.15 g (73%) of 4-(1H-imidazol-4-yl)-benzaldehyde as a yellow solid which was used without further purification: (DMSO-d6) δ 7.84-7.79 (m, 2H), 7.87 (d, 2H, J=8.4 Hz), 7.98 (d, 2H, J=8.2 Hz), 9.94 (s, 1H), 12.30-12.50 (br, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in 4:1 CHCl3/iPrOH
  3. filtrationThe resultant solids were filtered off
  4. washthe filtrate washed in turn with 5% Na2SO3/5% NaHCO3 solution, water, and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-f7123c19ca694f82b7c969a3eeef6f85
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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