2-Nitroaniline → 4-Bromo-2-nitroaniline

HRID 655431Notes

Reaction equation

HRID 655431 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].C1C(=O)N([Br:18])C(=O)C1>CC(O)=O.O>[Br:18][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1

Participants

5

Reactant 2

HCID 69462-NitroanilineHCID 67184N-bromobutanimide

Product 1

HCID 701324-Bromo-2-nitroanilineYield 76.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 2-nitroaniline (10.0 g, 72.462 mmol) in AcOH (50 mL) was added NBS (12.0 g, 72.463 mmol) at 0° C. under a N2 atmosphere. The reaction mixture was stirred at 40° C. for 30 min. After completion of starting material (monitored by TLC), reaction mixture was diluted with water and a white precipitate was formed. After filtration, the crude solid was recrystalised from n-hexanes to afford 4-bromo-2-nitroaniline (12 g, 76%), as a brown solid.

Workup

  1. customAfter completion of starting material (monitored by TLC), reaction mixture
  2. customa white precipitate was formed
  3. filtrationAfter filtration
  4. customthe crude solid was recrystalised from n-hexanes

Sources & evidence

ORD record
ord-670a00cf1f1243c4ad0d0414e68394d8
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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