Phenol → 3-Chloro-5-iodoaniline

HRID 2296517Notes

Reaction equation

HRID 2296517 reaction equation
Br[C:2]1[C:8]([I:9])=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:10].C1(O)C=CC=CC=1.I.[H][H]>>[Cl:10][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([I:9])[CH:2]=1)[NH2:6]

Participants

5

Reactant 4

HCID 996PhenolHCID 24841Hydrogen iodideHCID 20472918HCID 20472918, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 151684493-Chloro-5-iodoanilineYield 90%

Procedure

55.5 parts of 4-bromo-3-chloro-5-iodoaniline, 250 parts of phenol, 8 parts of hydroiodic acid (57% strength) and 15 parts of ruthenium-on-charcoal catalyst (5% strength) are reacted with hydrogen under a pressure of 23 to 47 bars and at 145° C., during the course of 2 hours, whilst stirring. After the usual working up, 38 parts of 3-chloro-5-iodo-aniline are obtained. Yield: 90% of theory.

Sources & evidence

ORD record
ord-9cf97ab399b04d638639b3895dd121ba
Source dataset
uspto-grants-1984_01
Patent number
US04429156

Reaction notes

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