Water → 4-{[4-(Trifluoromethyl)phenyl]sulfanyl}aniline

HRID 49435

Reaktionsgleichung

Reaktionsgleichung von HRID 49435
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1.CC(C)([O-])C.[K+].O>CS(C)=O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([S:19][C:16]2[CH:17]=[CH:18][C:13]([NH2:12])=[CH:14][CH:15]=2)=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 145104-AminothiophenolHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 221751604-{[4-(Trifluoromethyl)phenyl]sulfanyl}aniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 4-fluorobenzotrifluoride (9.85 g) and 4-aminothiophenol (7.51 g) in DMSO (60 mL), cooled in an ice bath, was added in one portion potassium t-butoxide (6.73 g). The resulting mixture was stirred at 0° C. for 10 minutes, then at 60° C. overnight. After cooling, the mixture was poured into water (600 mL) and the resulting mixture extracted with ether (2×200 mL). The organic phase was washed with 2N sodium hydroxide (50 mL), then with water (50 mL). After drying (MgSO4), the solvent was evaporated to give a brown solid. Recrystallization from hexane gave the title aniline as a yellow solid, m.p. 97-99° C.

Aufarbeitung

  1. customat 60° C.
  2. customovernight
  3. temperatureAfter cooling
  4. extractionthe resulting mixture extracted with ether (2×200 mL)
  5. washThe organic phase was washed with 2N sodium hydroxide (50 mL)
  6. dry with materialAfter drying (MgSO4)
  7. customthe solvent was evaporated
  8. customto give a brown solid
  9. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-2d142e8e4d7946b1ad94f4488202a711
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706740B2

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