Hydrochloric Acid → 5-Amino-2-methoxybenzotrifluoride

HRID 649830

Reaktionsgleichung

Reaktionsgleichung von HRID 649830
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].Cl>C(O)C.O.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]([F:13])([F:14])[F:15]

Komponenten

6

Edukt 2

HCID 313Hydrochloric AcidHCID 695624-Nitro-2-(trifluoromethyl)anisole

Produkt 1

HCID 6007055-Amino-2-methoxybenzotrifluoride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A suspension of 4-methoxy-3-trifluoromethyl-nitrobenzene (2.2 g) and iron powder (1.68 g) in ethanol (35 mL) and water (15 mL) is treated with a solution of concentrated hydrochloric acid (0.42 mL) in ethanol (6 mL) and water (3 mL) and the mixture is heated to reflux for approximately 1 hour. The mixture is then cooled, filtered, and concentrated under reduced pressure. The resulting oil is dissolved in ethyl acetate and extracted three times with 5% aqueous hydrochloric acid. The pooled acidic extracts are then cooled in an ice bath and basified with solid potassium carbonate, then extracted with ethyl acetate. These organic extracts are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure, then passed through a short column of silica gel (ethyl acetate is used as the eluant) to provide the desired compound as an amber oil.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux for approximately 1 hour
  3. temperatureThe mixture is then cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting oil is dissolved in ethyl acetate
  7. extractionextracted three times with 5% aqueous hydrochloric acid
  8. temperatureThe pooled acidic extracts are then cooled in an ice bath
  9. extractionextracted with ethyl acetate
  10. washThese organic extracts are washed with saturated aqueous sodium chloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4d1a94bb82564ed5bd47bbf9850f6094
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271236B1

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