2-Fluorotoluene → Bis(trifluoromethane)sulfonimide

HRID 1761820Notes

Reaction equation

HRID 1761820 reaction equation
[F:1][N:2]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[S:3]([C:6]([F:9])([F:8])[F:7])(=[O:5])=[O:4].FC1C=CC=CC=1C.FC1C=C(C)C=CC=1.FC1C=CC(C)=CC=1>C1(C)C=CC=CC=1>[F:1][N:2]([S:3]([C:6]([F:9])([F:7])[F:8])(=[O:5])=[O:4])[S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11].[NH:2]([S:3]([C:6]([F:9])([F:7])[F:8])(=[O:5])=[O:4])[S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 72412-FluorotolueneHCID 9603p-FluorotolueneHCID 9606m-FluorotolueneHCID 9796313Methanesulfonamide, N,1,1,1-tetrafluoro-N-[(trifluoromethyl)sulfonyl]-

Product 2

HCID 157857Bis(trifluoromethane)sulfonimideHCID 9796313Methanesulfonamide, N,1,1,1-tetrafluoro-N-[(trifluoromethyl)sulfonyl]-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  1. customensues near 22° C

Sources & evidence

ORD record
ord-66004bdc69f8469fb9e59b8ea991b7d5
Source dataset
uspto-grants-1989_05
Patent number
US04828764

Reaction notes

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