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

Participants

Reaction Steps

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)).

Provenance & Evidence