Potassium Hydroxide → 4-Bromo-2,6-difluoroaniline

HRID 1086394Notes

Reaction equation

HRID 1086394 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:5]=1[NH2:6].[OH-].[K+]>C(Cl)(Cl)Cl>[Br:1][C:9]1[CH:10]=[C:4]([F:3])[C:5]([NH2:6])=[C:7]([F:11])[CH:8]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24408BromineHCID 796472,6-Difluoroaniline

Product 1

HCID 6101914-Bromo-2,6-difluoroanilineYield 78.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

300 g of bromine was added drop-wise to 231 g of 2,6-difluoroaniline dissolved in 400 ml of chloroform. The mixture was refluxed for one hour and the reaction solution was poured into an aqueous 10% solution of potassium hydroxide. The potassium hydroxide was extracted with chloroform and the organic layer was washed with an aqueous 10% solution of potassium hydroxide and water. The chloroform was distilled off and the residue was distilled under reduced pressure (bp: 70°-80° C./4 mmHg) and recrystallized from hexane, to yield 292 g of 4-bromo-2,6-difluoroaniline.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. extractionThe potassium hydroxide was extracted with chloroform
  3. washthe organic layer was washed with an aqueous 10% solution of potassium hydroxide and water
  4. distillationThe chloroform was distilled off
  5. distillationthe residue was distilled under reduced pressure (bp: 70°-80° C./4 mmHg)
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-1cf7a60f4c0c43cda0521228a599fa24
Source dataset
uspto-grants-1991_07
Patent number
US05030382

Reaction notes

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