Water → 4-Bromo-2-nitroaniline

HRID 992059Notes

Reaction equation

HRID 992059 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])([O-:3])=[O:2].C1C(=O)N([Br:18])C(=O)C1.O>CC(O)=O>[Br:18][C:8]1[CH:7]=[CH:6][C:5]([NH2:10])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 69462-NitroanilineHCID 67184N-bromobutanimide

Product 1

HCID 701324-Bromo-2-nitroanilineYield 93.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-nitro-phenylamine (13.8 g, 100 mmol) in HOAc (150 mL) was added NBS (18 g, 101 mmol). The reaction mixture was stirred and heated to reflux over 1 hour. The cooled reaction mixture was poured into H2O (1000 mL) and stirred for 15 minutes. The resulting orange slurry was filtered and washed with H2O (300 mL) affording a 20.26 g (93%) of the title compound as a bright orange solid.

Workup

  1. temperatureheated
  2. temperatureto reflux over 1 hour
  3. customThe cooled reaction mixture
  4. stirringstirred for 15 minutes
  5. filtrationThe resulting orange slurry was filtered
  6. washwashed with H2O (300 mL)

Sources & evidence

ORD record
ord-e18fe3a11014440f90adb51c4478f16c
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

Loading…