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

HRID 1639190Notes

Reaction equation

HRID 1639190 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[Br:10]Br.[OH-].[K+]>C(Cl)(Cl)Cl>[Br:10][C:7]1[CH:8]=[C:2]([F:1])[C:3]([NH2:4])=[C:5]([F:9])[CH:6]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24408BromineHCID 796472,6-Difluoroaniline

Product 1

HCID 6101914-Bromo-2,6-difluoroanilineYield 78.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

100 g of 2,6-difluoroaniline was dissolved in 180 ml of chloroform and 140 g of bromine was added dropwise. After one hour of reflux, the resulting solution was poured into a solution of 10% potassium hydroxide. The mixture was extracted with chloroform and the organic layer was washed with a solution of 10% potassium hydroxide in water. After the chloroform was removed by distillation, the residue was distilled under reduced pressure (bp 70° to 80° C. at 4 mmHg) and recrystallized with hexane to yield 127 g of 4-bromo-2,6-difluoroaniline.

Workup

  1. temperatureAfter one hour of reflux
  2. extractionThe mixture was extracted with chloroform
  3. washthe organic layer was washed with a solution of 10% potassium hydroxide in water
  4. customAfter the chloroform was removed by distillation
  5. distillationthe residue was distilled under reduced pressure (bp 70° to 80° C. at 4 mmHg)
  6. customrecrystallized with hexane

Sources & evidence

ORD record
ord-b619ecca41204f218937927869a5784d
Source dataset
uspto-grants-1989_11
Patent number
US04883609

Reaction notes

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