Water → HCID 118452636, Verbindung

HRID 1773242

Reaktionsgleichung

Reaktionsgleichung von HRID 1773242
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[C:6]([C:15]([CH3:17])=[CH2:16])[CH:5]=1)([O-])=O.O>C1(C)C=CC=CC=1.Cl.[Fe]>[CH2:16]=[C:15]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][C:11]([F:12])([F:14])[F:13])[NH2:1])[CH3:17]

Komponenten

6

Edukt 2

HCID 962WaterHCID 1184526474-Nitro-2-(prop-1-en-2-yl)-1-(trifluoromethoxy)benzene

Produkt 1

HCID 118452636HCID 118452636, VerbindungAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23925IronKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-nitro-2-(prop-1-en-2-yl)-1-(trifluoromethoxy)benzene (275 mg, 1.11 mmol) in toluene (9.85 mL) was added iron (1.24 g, 22.25 mmol) and concentrated HCl (3.38 μL, 0.11 mmol) (3 drops). The mixture was stirred vigorously under reflux and water (0.20 mL, 11.13 mmol) was added and the r×n was stirred at reflux for 2 hr. The crude mixture was filtered through celite and concentrated under reduced pressure. The crude was diluted with EtOAc and dried with Na2SO4, filtered and concentrated under reduced pressure to give 3-(prop-1-en-2-yl)-4-(trifluoromethoxy)aniline (230 mg). LCMS retention time=1.46 minutes (LC method 5); MS (m+1)=218.2.

Aufarbeitung

  1. temperatureunder reflux
  2. stirringthe r×n was stirred
  3. temperatureat reflux for 2 hr
  4. filtrationThe crude mixture was filtered through celite and
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude was diluted with EtOAc
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3a87f898d71d47efb17e856a27b9102b
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255093B2

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