Tin tetrachloride → 4-(2,5-Dichlorophenoxy)-3-fluoroaniline

HRID 33759

Reaktionsgleichung

Reaktionsgleichung von HRID 33759
[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[F:14].[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[F:14]

Komponenten

5

Edukt 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 597980461-(2,5-Dichloro-phenoxy)-2-fluoro-4-nitro-benzene

Produkt 1

HCID 289727064-(2,5-Dichlorophenoxy)-3-fluoroaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1-(2,5-dichloro-phenoxy)-2-fluoro-4-nitro-benzene (0.5 g, 1.7 mmol) and tin chloride (1.57 g, 8.3 mmol) in 30 ml of anhydrous ethanol was heated to 70° C. under argon and stirred for 4 hours. The solution was allowed to cool and then poured into ice. The solution was made slightly basic (pH 7-8) by addition of saturated aqueous sodium bicarbonate solution, then extracted with ethyl acetate. The organic phase was thoroughly washed with brine and dried treated with anhydrous sodium sulfate. Evaporation of the solvent left a yellow oily product which was used for the next step without further purification.

Aufarbeitung

  1. temperatureto cool
  2. additionpoured into ice
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was thoroughly washed with brine
  5. customdried
  6. additiontreated with anhydrous sodium sulfate
  7. customEvaporation of the solvent
  8. waitleft a yellow oily product which
  9. customwas used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3f16de5a631343f9ab6d061ff9289df8
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429667B2

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