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2-(Trifluoromethyl)aniline → 4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]-2-(trifluoromethyl)benzenamine

HRID 590937
ノート
印刷プレビュー

反応式

HRID 590937 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+].[F:25][C:26]([F:35])([F:34])[C:27](I)([F:32])[C:28]([F:31])([F:30])[F:29]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>[F:32][C:27]([C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:9]=1)([C:28]([F:31])([F:30])[F:29])[C:26]([F:35])([F:34])[F:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 69222-(Trifluoromethyl)anilineHCID 24489Sodium DithioniteHCID 33978Perfluoroisopropyl iodideHCID 516892Sodium Bicarbonate

生成物 1

HCID 582974594-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]-2-(trifluoromethyl)benzenamine収率 30%

試薬・触媒・溶媒 3

HCID 94433
Tetrabutylammonium hydrogen sulfate
触媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

100 g (0.608 mol) of 2-(trifluoromethyl)aniline, 131 g (0.639 mol) of 85% sodium hydrosulfite, and 20.9 g (0.0608 mol) of tetrabutylammonium hydrogen sulfate were charged to a mixed solution of 1500 ml of ethyl acetate and 1500 ml of water, and 53.9 g (0.639 mol) of sodium hydrogen carbonate was added thereto. 198 g (0.669 mol) of heptafluoroisopropyl iodide was added dropwise thereto at room temperature, followed by stirring at room temperature for 6 hours. After the liquid separation, the solvent of the organic layer was evaporated under reduced pressure, and 500 ml of ethyl acetate was charged thereto. 160 g (0.608 mol) of a 4 M hydrogen chloride/ethyl acetate solution was added dropwise thereto, followed by stirring at room temperature for 30 minutes, and then stirring at 5° C. for 1 hour. After the filtration, the filtrate was washed with water and a saturated aqueous sodium hydrogen carbonate in this order, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=10:1) to prepare 60.0 g (yield 30%) of a target compound.

後処理

  1. additionwas added
  2. customat room temperature
  3. customAfter the liquid separation
  4. customthe solvent of the organic layer was evaporated under reduced pressure, and 500 ml of ethyl acetate
  5. additionwas charged
  6. addition160 g (0.608 mol) of a 4 M hydrogen chloride/ethyl acetate solution was added dropwise
  7. stirringby stirring at room temperature for 30 minutes
  8. stirringstirring at 5° C. for 1 hour
  9. filtrationAfter the filtration
  10. washthe filtrate was washed with water
  11. dry with materiala saturated aqueous sodium hydrogen carbonate in this order, and then dried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customThe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-bf61d917241b4ee79e6bc062c655ccc0
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09237745B2

反応ノート

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