1-Chloro-2-iodo-5-methoxy-4-nitrobenzene → 4-Chloro-5-iodo-2-methoxyaniline

HRID 588774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588774
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][C:3]=1[I:13]>C(O)(=O)C.O.[Fe]>[Cl:1][C:2]1[C:3]([I:13])=[CH:4][C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Komponenten

5

Edukt 1

HCID 904558901-Chloro-2-iodo-5-methoxy-4-nitrobenzene

Produkt 1

HCID 917583774-Chloro-5-iodo-2-methoxyanilineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 1-chloro-2-iodo-5-methoxy-4-nitrobenzene (113 g, 0.361 mol) in acetic acid (1 L) and water (50 mL) at 50° C., Fe (50.5 g, 0.903 mol) was added and the resulting mixture was stirred at 50° C. for 2 h. The mixture was allowed to cool to room temperature and then poured into ice-water. The precipitate was collected by filtration and rinsed with water. This crude product was dissolved with ethyl acetate (1 L) and filtered. The filtrate was washed with saturated NaHCO3 solution and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product (87 g, 85% yield).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationThe precipitate was collected by filtration
  3. washrinsed with water
  4. dissolutionThis crude product was dissolved with ethyl acetate (1 L)
  5. filtrationfiltered
  6. washThe filtrate was washed with saturated NaHCO3 solution and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3b40ab883a254c87ad142c9c418d6fe1
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227978B2

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