Water → 4-Bromo-2,6-dinitroaniline

HRID 539144

Reaktionsgleichung

Reaktionsgleichung von HRID 539144
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:5]=1[NH2:6])([O-:3])=[O:2].[Br:14]Br.O>C(O)(=O)C>[Br:14][C:9]1[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([NH2:6])=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24408BromineHCID 690702,6-Dinitroaniline

Produkt 1

HCID 37466084-Bromo-2,6-dinitroanilineAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A stirred suspension of 2,6-dinitroaniline (5 g, 27.3 mmol) in glacial acetic acid (50 mL) was added bromine (1.5 mL, 30 mmol) dropwise and heated at 120° C. for 2 h. After cooling to ambient temperature, the resultant mixture was poured into water (50 mL). The precipitate solid was collected by filtration and washed with water then dried in-vacuo. The solid was re-dissolved in EtOAC, washed with water and saturated brine. The organic layer was collected and concentrated in-vacuo to give the desired product (6.88 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.37 (br s, 2H), 8.58 (s, 2H).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. filtrationThe precipitate solid was collected by filtration
  3. washwashed with water
  4. customthen dried in-vacuo
  5. dissolutionThe solid was re-dissolved in EtOAC
  6. washwashed with water and saturated brine
  7. customThe organic layer was collected
  8. concentrationconcentrated in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ff3a7afd5d754ae2850fc41f1d3f7be1
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865912B2

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