2-Fluorotoluene → Bis(trifluoromethane)sulfonimide

Participants

Reaction Steps

By vacuum transfer, FN(SO2CF3)2 (1.7 mmol) was added to 2.0 ml of toluene at -196° C. The mixture was warmed to room temperature and agitated by hand. A slow color change ensues near 22° C. After 10 hours, 19F NMR shows the presence of 2-fluorotoluene (74%), 3-fluorotoluene (4%) and 4-fluorotoluene (21%). The ratio of unreacted FN(SO2CF )3)2 to the HN(SO2CF3)2 formed in the reaction indicates an 80% conversion to the monofluorotoluene isomers. No other fluorine containing products are observed by NMR.

Provenance & Evidence