Iodine → 3,5-Dichloroaniline

HRID 2296518Notes

Reaction equation

HRID 2296518 reaction equation
C1(O)C=CC=CC=1.II.ClC1C(Cl)=C(C=CC=1)N(Cl)Cl.Cl[C:22]1[C:27]([NH2:28])=[C:26](Cl)[C:25]([Cl:30])=[C:24](Cl)[C:23]=1[Cl:32].[H][H]>O.[Ta]>[Cl:30][C:25]1[CH:26]=[C:27]([CH:22]=[C:23]([Cl:32])[CH:24]=1)[NH2:28]

Participants

7

Reactant 4

HCID 807IodineHCID 996PhenolHCID 131713377HCID 131713377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122813,5-DichloroanilineYield 94%

Reagents, catalysts & solvents 2

HCID 23956TantalumCatalystHCID 962WaterSolvent

Procedure

200 parts of phenol, 5.7 parts of iodine, 197 parts of a tetrachloroaniline/pentachloroaniline mixture according to the data in Example 3, and 20 parts of ruthenium-on-charcoal catalyst (5% strength) are subjected to a hydrogenating dehalogenation in a tantalum autoclave at 175° C. with hydrogen under a maximum pressure of 50 bars. In the working up process, the hot mixture is dissolved in 450 parts by volume of water at 100° C., the catalyst is separated off through a suction filter and the filtrate is neutralised with sodium hydroxide solution. 3,5-Dichloroaniline and phenol are separated off from the water phase with the aid of toluene, and the organic solution is distilled. After distilling off toluene and water, the phenol is separated off from the 3,5-dichloroaniline by distillation and can be used again. The crude 3,5-dichloroaniline which remains is purified by distillation over a simple distillation bridge. 132 parts of 98% strength 3,5-dichloroaniline is obtained; yield 94% of theory.

Workup

  1. customthe catalyst is separated off through a suction
  2. filtrationfilter
  3. custom3,5-Dichloroaniline and phenol are separated off from the water phase with the aid of toluene
  4. distillationthe organic solution is distilled
  5. distillationAfter distilling off toluene and water
  6. customthe phenol is separated off from the 3,5-dichloroaniline by distillation
  7. distillationThe crude 3,5-dichloroaniline which remains is purified by distillation over a simple distillation bridge

Sources & evidence

ORD record
ord-aaa605ceb0bc44c9befeb5d3b8f60cb9
Source dataset
uspto-grants-1984_01
Patent number
US04429156

Reaction notes

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