Potassium Iodide → 1,4-Dibromo-2-iodobenzene

HRID 1045289Notes

Reaction equation

HRID 1045289 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:3]=1N.N([O-])=O.[Na+].[I-:14].[K+].S([O-])(O)=O.[Na+]>Cl.C(Cl)Cl>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:3]=1[I:14]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 771982,5-DibromoanilineHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 134063481,4-Dibromo-2-iodobenzeneYield 73%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2,5-Dibromoaniline 10 g was dispersed in diluted hydrochloric acid (concentrated hydrochloric acid 40 ml+water 30 ml), and an aqueous solution of NaNO2 3 g was dropwise added thereto at 0° C. The reaction solution was stirred for 40 minutes and then dropwise added at room temperature to an aqueous solution of potassium iodide 60 g which was separately prepared. After stirring at room temperature for 2 hours, methylene chloride and a small amount of sodium hydrogensulfite were added thereto, and the organic layer was extracted. The organic layer was washed with a 10% sodium hydrogensulfite aqueous solution and saturated brine and dried on anhydrous sodium sulfate, and then the solvent was distilled off. The product was refined by silica gel chromatography, whereby targeted 2,5-dibromoiodobenzene 10.5 g (yield: 73%) was obtained in the form of white crystal.

Workup

  1. customat 0° C
  2. customwas separately prepared
  3. stirringAfter stirring at room temperature for 2 hours
  4. extractionthe organic layer was extracted
  5. washThe organic layer was washed with a 10% sodium hydrogensulfite aqueous solution and saturated brine
  6. dry with materialdried on anhydrous sodium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c3146c55c76044038c473bc6fc978f0a
Source dataset
uspto-grants-2013_10
Patent number
US08568902B2

Reaction notes

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