Hydrogen Peroxide → Ethyl 4-amino-3-iodobenzoate

HRID 2102846Notes

Reaction equation

HRID 2102846 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-bce1c86350544abdab728a2e3686792a
Source dataset
uspto-grants-2009_08
Patent number
US07576079B2

Reaction notes

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