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

HRID 1991725Notes

Reaction equation

HRID 1991725 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:11]Br>CC(O)=O>[Br:11][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[NH2:10]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 24408Bromine

Product 1

HCID 25840Benzenamine, 2-bromo-4-nitro-Yield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-nitro-phenylamine (50 g, 0.36 mol) in AcOH (500 mL) was added Br2 (60 g, 0.38 mol) dropwise at 5° C. The mixture was stirred for 30 min at that temperature. The insoluble solid was collected by filtration and basified with saturated aqueous NaHCO3 to pH 7. The aqueous phase was extracted with EtOAc (300 mL×3). The combined organic layers were dried and evaporated under reduced pressure to obtain compound 2-bromo-4-nitroaniline (56 g, 72%), which was directly used in the next step.

Workup

  1. filtrationThe insoluble solid was collected by filtration
  2. extractionThe aqueous phase was extracted with EtOAc (300 mL×3)
  3. customThe combined organic layers were dried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0b77051837a1446eb965b7ad299e16f6
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

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