Sodium Dithionite → 1-(1-Bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)aniline

HRID 70808

Reaktionsgleichung

Reaktionsgleichung von HRID 70808
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].[Br:12][C:13]([F:22])([F:21])[C:14](Br)([F:19])[C:15]([F:18])([F:17])[F:16].C(=O)([O-])O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(OC)(C)(C)C.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:12][C:13]([F:22])([F:21])[C:14]([C:5]1([C:4]([O:3][CH:2]([F:11])[F:1])=[CH:10][CH:9]=[CH:8][CH2:7]1)[NH2:6])([F:19])[C:15]([F:18])([F:17])[F:16]

Komponenten

8

Edukt 4

HCID 24489Sodium DithioniteHCID 695791,2-Dibromo-1,1,2,3,3,3-hexafluoropropaneHCID 516892Sodium BicarbonateHCID 9346202-(Difluoromethoxy)aniline

Produkt 1

HCID 866729651-(1-Bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)anilineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

2-(Difluoromethoxy)aniline (1280 mg) and 1,2-dibromo-1,1,2,3,3,3-hexafluoropropane (8610 mg) were dissolved in tert-butylmethyl ether (30 ml) and water (30 ml), and added with tetrabutylammonium hydrogen sulfate salt (270 mg), sodium hydrogen carbonate (2030 mg) and sodium dithionite (4200 mg) in order. The mixture was stirred vigorously at room temperature for 2 days. The reaction solution was extracted twice with ethyl acetate. The organic phases were combined and washed with water, and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the solvent was removed by distillation under the reduced pressure. The resulting residues were purified by column chromatography to obtain 1-(1-bromo-1,1,2,3,3,3-hexafluoropropan-2-yl)-6-(difluoromethoxy)aniline (810 mg, 26%).

Aufarbeitung

  1. extractionThe reaction solution was extracted twice with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe solvent was removed by distillation under the reduced pressure
  6. customThe resulting residues were purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f84e546fae6a492f91ed5477249a305d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822691B2

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