HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Fluorotoluene → Bis(trifluoromethane)sulfonimide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Fluorotoluene | HCID 7241 | — |
| Reactant | p-Fluorotoluene | HCID 9603 | — |
| Reactant | m-Fluorotoluene | HCID 9606 | — |
| Reactant | Methanesulfonamide, N,1,1,1-tetrafluoro-N-[(trifluoromethyl)sulfonyl]- | HCID 9796313 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Bis(trifluoromethane)sulfonimide | HCID 157857 | — |
| Product | Methanesulfonamide, N,1,1,1-tetrafluoro-N-[(trifluoromethyl)sulfonyl]- | HCID 9796313 | — |
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(SO2CF3)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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04828764 |
| Source dataset | uspto-grants-1989_05 |
| ORD ID | ord-66004bdc69f8469fb9e59b8ea991b7d5 |
| Source note | uspto-grants-1989_05 |