Sodium Dithionite → 3-Isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline

HRID 2388624Notes

Reaction equation

HRID 2388624 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])[CH:2]([CH3:4])[CH3:3].[F:12][C:13]([F:22])([F:21])[C:14](I)([F:19])[C:15]([F:18])([F:17])[F:16].C(=O)([O-])O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.COC(C)(C)C.O>[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[C:14]([F:19])([C:15]([F:18])([F:17])[F:16])[C:13]([F:22])([F:21])[F:12])[NH2:8])[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 24489Sodium DithioniteHCID 33978Perfluoroisopropyl iodideHCID 516892Sodium BicarbonateHCID 190247993-Isobutylaniline

Product 1

HCID 866190023-Isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]anilineYield 47%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8058HexaneSolventHCID 23212559water MeOtBuSolvent

Procedure

3-Isobutylaniline (14.9 g, 0.1 mol) was diluted in a 300 ml mixed solvent of tert-butyl methyl ether-water (1:1), followed by sequentially adding heptafluoroisopropyl iodide (29.6 g, 0.1 mol), tetrabutylammonium hydrogensulfate (3.4 g, 0.01 mol), sodium hydrogen carbonate (8.4 g, 0.1 mol) and sodium dithionite (17 g, 0.1 mol) and stirring overnight at room temperature. The reaction solution was diluted with hexane, followed by washing twice with a 3N HCl solution, and with aqueous sodium bicarbonate and a saturated brine. The solution was dried over magnesium sulfate and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=6:1) to obtain 14.9 g of the desired compound.

Workup

  1. washby washing twice with a 3N HCl solution
  2. dry with materialThe solution was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified

Sources & evidence

ORD record
ord-482b76009f7c40fcaf28a98a30b9208a
Source dataset
uspto-grants-2012_09
Patent number
US08269045B2

Reaction notes

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