Aniline → 4-(Undecafluorocyclohexyl)aniline

HRID 70817Notes

Reaction equation

HRID 70817 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:8][C:9]1([F:25])[C:14]([F:16])(I)[C:13]([F:18])([F:17])[C:12]([F:20])([F:19])[C:11]([F:22])([F:21])[C:10]1([F:24])[F:23].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(OC)(C)(C)C.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:8][C:9]1([F:25])[C:14]([F:16])([C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[C:13]([F:18])([F:17])[C:12]([F:19])([F:20])[C:11]([F:21])([F:22])[C:10]1([F:23])[F:24]

Participants

8

Reactant 4

HCID 6115AnilineHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 2759367Iodoperfluorocyclohexane

Product 1

HCID 866729764-(Undecafluorocyclohexyl)anilineYield 68%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Aniline (1.0 g) was dissolved in tert-butylmethyl ether (15 ml) and water (15 ml), and added with undecafluoroiodocyclohexane (5.5 g), sodium dithionite (2.3 g), sodium hydrogen carbonate (1.1 g) and tetrabutylammonium hydrogen sulfate (0.46 g) in order. The resulting mixture was stirred vigorously at room temperature for 18 hours. After separating the reaction solution, the aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and washed with 2N hydrochloric acid and sodium hydrogen carbonate solution in order, and dried over anhydrous magnesium sulfate, The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain 4-(undecafluorocyclohexyl)aniline (2.7 g, yield 68%).

Workup

  1. customAfter separating the reaction solution
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. washwashed with 2N hydrochloric acid and sodium hydrogen carbonate solution in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  6. distillationthe solvent was distilled off under the reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-45f62759dcd5421bb66c8fd1b768bbe7
Source dataset
uspto-grants-2014_09
Patent number
US08822691B2

Reaction notes

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