Potassium Iodide → 5-Chloro-2-hydroxy-3-iodobenzaldehyde

HRID 2120060Notes

Reaction equation

HRID 2120060 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[I:11]N1C(=O)CCC1=O.IC1C=C(Br)C=C(C=O)C=1O.BrC1C=C(C=O)C(O)=CC=1.[I-].[K+].CC1C=CC(S(NCl)(=O)=O)=CC=1>CN(C=O)C.C(#N)C>[I:11][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:10]

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 124815-Chloro-salicylaldehydeHCID 31388TosylchloramideHCID 728635-BromosalicylaldehydeHCID 120273N-IodosuccinimideHCID 27166955-Bromo-2-hydroxy-3-iodobenzaldehyde

Product 1

HCID 37725455-Chloro-2-hydroxy-3-iodobenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Some product precipitates and is recovered by filtration. The remainder is recovered by diluting the filtrate with water and isolating the precipitate. Combining the solids and drying gives 3-chloro-5-bromo-2-hydroxybenzaldehyde. 3-iodo-5-chlorosalicylaldehyde was prepared by reacting 5-chlorosalicylaldehyde with N-iodosuccinimide in DMF and subjecting the reaction mixture to conventional work-up conditions. 3-iodo-5-bromosalicylaldehyde can be prepared by reacting 5-bromosalicylaldehyde in acetonitrile with potassium iodide and chloramine T. Conventional work-up gives a material that when treated with hexanes gives the desired 3-iodo-5-chlorosalicylaldehyde.

Workup

  1. custom3-iodo-5-chlorosalicylaldehyde was prepared
  2. customConventional work-up gives a material that when

Sources & evidence

ORD record
ord-c15464c3e51a476f995215ebaed46267
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

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