Ammonium Chloride → 3,5-Dibromoaniline

HRID 429138Notes

Reaction equation

HRID 429138 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[C:6]([Br:8])[CH:7]=1.[Cl-].[NH4+]>CO.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Br:8])[CH:7]=1)[NH2:9]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 2387111,3-dibromo-5-nitrobenzene

Product 1

HCID 2215123,5-DibromoanilineYield 87.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3,5-dibromo nitrobenzene (J. Amer. Chem Soc., 1950, 72, 793) (1.0 g, 3.6 mmol) in methanol (30 ml) was added in portions to a stirred mixture of iron powder (0.52 g, 9.3 mmol) in a saturated solution of ammonium chloride (50 ml) at 60° C. The mixture was heated at reflux for 2 h, filtered and the filtrate extracted with dichloromethane (2×70 ml). The organic extract was dried (Na2SO4) and concentrated in vacuo to give the title compound (D7) as an oil (0.787 g, 87%), MH+ 250/252.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. extractionthe filtrate extracted with dichloromethane (2×70 ml)
  5. extractionThe organic extract
  6. dry with materialwas dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffae0db484724dad82df50d26e59158d
Source dataset
uspto-grants-2001_11
Patent number
US06316450B1

Reaction notes

Loading…