Hydrogen Bromide → 6-Iodo-4-trifluoromethyl-isatin

HRID 1369078Notes

Reaction equation

HRID 1369078 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[CH:6][C:7]([I:15])=[CH:8][C:9]=2[C:11]([F:14])([F:13])[F:12])[NH:4][C:3]1=[O:16].[OH2:18].Br>CO>[F:12][C:11]([F:14])([F:13])[C:9]1[CH:8]=[C:7]([I:15])[CH:6]=[C:5]2[C:10]=1[C:2](=[O:18])[C:3](=[O:16])[NH:4]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 12130817HCID 12130817, compound

Product 1

HCID 99973896-Iodo-4-trifluoromethyl-isatin

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 3,3-dibromo-4-trifluoromethyl-6-iodooxindole (35.11 g) prepared above was dissolved in MeOH (1200 mL) and H2O (300 mL) was added. The resulting mixture was heated at reflux for 3 hours and then aqueous 48% HBr (10 mL) was added. The solution was then heated at reflux for 27 hours. The MeOH solvent was removed in vacuo to give a brown/yellow solid. The solid was isolated by filtration, washing the collected solid with copious amounts of H2O. The solid was then dried overnight in a vacuum desiccator (NaOH as desiccant) to give the desired isatin as a light brown solid (20.8214 g, 95% (two steps)).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe solution was then heated
  4. temperatureat reflux for 27 hours
  5. customThe MeOH solvent was removed in vacuo
  6. customto give a brown/yellow solid
  7. customThe solid was isolated by filtration
  8. washwashing the collected solid with copious amounts of H2O
  9. dry with materialThe solid was then dried overnight in a vacuum desiccator (NaOH as desiccant)

Sources & evidence

ORD record
ord-dcd336a8da884a75b6746efef99c1e62
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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