4-Nitroaniline → Benzenamine, 2-bromo-4-nitro-

HRID 468328

Reaktionsgleichung

Reaktionsgleichung von HRID 468328
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:11]Br>CC(O)=O>[Br:11][C:9]1[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[NH2:8]

Komponenten

4

Edukt 2

HCID 74754-NitroanilineHCID 24408Bromine

Produkt 1

HCID 25840Benzenamine, 2-bromo-4-nitro-Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 4-nitro-aniline (25 g, 0.18 mol) in HOAc (150 mL) was added liquid Br2 (30 g, 0.19 mol) dropwise at room temperature. The mixture was stirred for 2 hours. The solid was collected by filtration and poured into water (1.00 mL), which was basified with sat. aq. NaHCO3 to pH 7 and extracted with EtOAc (300 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give 2-bromo-4-nitroaniline (30 g, 80%), which was directly used in the next step.

Aufarbeitung

  1. filtrationThe solid was collected by filtration
  2. additionpoured into water (1.00 mL), which
  3. extractionextracted with EtOAc (300 mL×3)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a0369510191143ca98024fbfeab51ce7
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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