Phenol → 3,5-Dichloroaniline

HRID 2296516Notes

Reaction equation

HRID 2296516 reaction equation
ClC1C(Cl)=C(C=CC=1)N(Cl)Cl.Cl[C:13]1[C:18]([NH2:19])=[C:17](Cl)[C:16]([Cl:21])=[C:15](Cl)[C:14]=1[Cl:23].C1(O)C=CC=CC=1.IC1C=CC=CC=1O.[H][H]>[Ta]>[Cl:21][C:16]1[CH:17]=[C:18]([CH:13]=[C:14]([Cl:23])[CH:15]=1)[NH2:19]

Participants

6

Reactant 4

HCID 996PhenolHCID 107842-IodophenolHCID 131713377HCID 131713377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122813,5-DichloroanilineYield 95%

Reagents, catalysts & solvents 1

HCID 23956TantalumCatalyst

Procedure

131 parts of a tetrachloroaniline/pentachloroaniline mixture, 200 parts of phenol and 10 parts of 2-iodophenol are reacted in the presence of 12.5 parts of ruthenium-on-charcoal catalyst (5%) in a tantalum autoclave with hydrogen under a pressure of from 29 to 50 bars at a maximum temperature of 165° C., during the course of 8 hours, whilst stirring. 87.5 parts of 3,5-dichloroaniline are obtained after working up the reaction mixture. Yield: 95% of theory.

Sources & evidence

ORD record
ord-f057ee883a8f4d76b614d1512210fc23
Source dataset
uspto-grants-1984_01
Patent number
US04429156

Reaction notes

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