Hydrogen Peroxide → Ethyl 4-amino-3-iodobenzoate

HRID 723631Notes

Reaction equation

HRID 723631 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[I:13]I.ClC1C=CC=CC=1.OO>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][C:12]=1[I:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 807IodineHCID 2337BenzocaineHCID 7964Chlorobenzene

Product 1

HCID 459320Ethyl 4-amino-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 4-aminobenzoate (15.00 g, 91 mmol) and iodine (11.80 g, 46.5 mmol) were mixed with water (80 mL) and chlorobenzene (4.60 g, 41 mmol). The mixture was stirred while the temperature was gradually raised to 90° C. over 30 min. Hydrogen peroxide (30%, 50 mL) was added over 10 h at 90° C. After stirring at that temperature for an additional 6 h, the mixture was cooled and the solution decanted from the residual solids. The solids were dissolved in DCM and the solution washed successively with sodium thiosulfate and brine. After drying (MgSO4), the solvent was removed under reduced pressure and the resulting brown solid was triturated with hexane to remove di-iodinated by-products. The desired compound was obtained as a brown solid (22.85 g, 86% yield).

Workup

  1. stirringAfter stirring at that temperature for an additional 6 h
  2. temperaturethe mixture was cooled
  3. customthe solution decanted from the residual solids
  4. dissolutionThe solids were dissolved in DCM
  5. washthe solution washed successively with sodium thiosulfate and brine
  6. dry with materialAfter drying (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customthe resulting brown solid was triturated with hexane
  9. customto remove di-iodinated by-products

Sources & evidence

ORD record
ord-ee173e08e4304272ac0e979f7a2bbc5c
Source dataset
uspto-grants-2006_11
Patent number
US07141574B2

Reaction notes

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