Aniline → 4-(Undecafluorocyclohexyl)aniline

HRID 70817ノート

反応式

HRID 70817 の反応式
[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]

参加物

8

反応物 4

HCID 6115AnilineHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 2759367Iodoperfluorocyclohexane

生成物 1

HCID 866729764-(Undecafluorocyclohexyl)aniline収率 68%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-45f62759dcd5421bb66c8fd1b768bbe7
出典データセット
uspto-grants-2014_09
特許番号
US08822691B2

反応ノート

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