Sodium trifluoromethanesulfinate → 1-Fluoro-2-(trifluoromethylsulfonyl)benzene

HRID 1920490Notes

Reaction equation

HRID 1920490 reaction equation
[O-:1][S:2]([C:5]([F:8])([F:7])[F:6])(=O)=[O:3].C1(C)C=C(C)C=C(C)C=1[I+][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[F:24].FC(F)(F)S([O-])=O.[Na+]>[Cu-]=O.CN(C)C=O>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1]

Participants

5

Reactant 2

HCID 23690734Sodium trifluoromethanesulfinateHCID 86637458HCID 86637458, compound

Product 1

HCID 157316611-Fluoro-2-(trifluoromethylsulfonyl)benzene

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Mesityl-2-fluorophenyl iodonium triflate (Sanford M et al. JACS, 2005, 127, 7330 and Widdowson, D. et al. Tetrahedron Letters 2000, 41, 5393.) (0.1 g, 0.204 mmol), sodium trifluoromethanesulfinate (0.035 g, 0.224 mmol) and copper(I) oxide (2.92 mg, 0.020 mmol) were weighed into a reactor equipped with a magnetic stir bar. N,N-dimethylformamide (1 mL) was added, the reactor was capped and heated at 25° C. for 24 hours. HPLC analysis of the crude reaction mixture indicated the formation of the title compound.

Workup

  1. customequipped with a magnetic stir bar
  2. customthe reactor was capped
  3. customHPLC analysis of the crude reaction mixture

Sources & evidence

ORD record
ord-12f501d81ec04c4389d831cce2a3e007
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

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