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

HRID 503328Notes

Reaction equation

HRID 503328 reaction equation
[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]

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-nitroaniline (50 g, 0.36 mol) in AcOH (500 mL) was added liquid 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 poured into EtOAc (200 mL). The mixture was basified with saturated aqueous NaHCO3 to pH 7. The organic layer was separated. The aqueous phase was extracted with EtOAc (300 mL×3). The combined organic layers were dried and evaporated under reduced pressure to give 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. additionpoured into EtOAc (200 mL)
  3. customThe organic layer was separated
  4. extractionThe aqueous phase was extracted with EtOAc (300 mL×3)
  5. customThe combined organic layers were dried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1c22109e66db49b5add6c8a01c004225
Source dataset
uspto-grants-2010_08
Patent number
US07776905B2

Reaction notes

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