Ammonium Chloride → 3-Bromo-5-fluoroaniline

HRID 1534096Notes

Reaction equation

HRID 1534096 reaction equation
[Cl-].[NH4+].[Br:3][C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([F:13])[CH:5]=1>O.[Fe]>[Br:3][C:4]1[CH:9]=[C:8]([CH:7]=[C:6]([F:13])[CH:5]=1)[NH2:10]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 150201571-Bromo-3-fluoro-5-nitrobenzene

Product 1

HCID 150201553-Bromo-5-fluoroanilineYield 58.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 29.0 g of iron powder and 20.0 g of ammonium chloride in 50 ml of water was heated to 90° C. with vigorous stirring. To this was added 24.0 g of 1-bromo-3-fluoro-5-nitrobenzene portionwise. The mixture was refluxed for 4 hours, cooled to room temperature and filtered to remove insoluble matter. The insoluble matter and the filtrate were extracted, respectively, with ethyl acetate. Both extracts were combined together and evaporated in vacuo to give 12.1 g of the title compound. Vacuum distillation of a portion thereof gave an analytical sample boiling at 103.0°-105.0° C. /7 mm Hg.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. customto remove insoluble matter
  5. extractionThe insoluble matter and the filtrate were extracted
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-58060f5cf34e41b584de885904424880
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

Loading…