Water → 4-Bromo-3-chloro-2-nitroaniline

HRID 1429208Notes

Reaction equation

HRID 1429208 reaction equation
[Cl:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:12]N1C(=O)CCC1=O.O>C(O)(=O)C>[Br:12][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 1010683-Chloro-2-nitroaniline

Product 1

HCID 265991564-Bromo-3-chloro-2-nitroanilineYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Chloro-2-nitroaniline (5.00 g, 29.0 mmol) was dissolved in glacial acetic Acid (258 mL). N-Bromosuccinimide (5.06 g, 28.4 mmol) was added and the resulting mixture was refluxed for 1 hour. The reaction was cooled to room temperature and poured into water to give a precipitate that was filtered, rinsed with water and dried to constant weight to give the title compound (4.78 g, 67%). 1H NMR (400 MHz, CDCL3) δ ppm 7.46 (d, J=9.0, 1H), 6.64 (d, J=9.0, 1H), 4.74 (s, 2H).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. customto give a precipitate that
  3. filtrationwas filtered
  4. washrinsed with water
  5. customdried to constant weight

Sources & evidence

ORD record
ord-60eb2b8e6aea4665be512051a3418fee
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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