Potassium Iodide → 4-Chloro-2-iodo-1-nitrobenzene

HRID 460430Notes

Reaction equation

HRID 460430 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=1N)([O-:3])=[O:2].N([O-])=O.[Na+].[I-:16].[K+]>Cl.O>[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=1[I:16])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 742185-Chloro-2-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 114261004-Chloro-2-iodo-1-nitrobenzene

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 2-nitro-5-chloroaniline (5.00 g) in conc. hydrochloric acid (30 ml) under cooling with ice, was added a solution of sodium nitrite (2.10 g) in water (10 ml) dropwise and the mixture was stirred for 30 minutes. Under cooling with ice, to this solution was added a solution of potassium iodide (5.30 g) in water (20 ml) dropwise and the mixture was stirred for 1 hour at room temperature. The solid that appeared was collected by filtration and was dissolved in ethyl acetate and was dried and concentrated to give a crude product of the title compound. It was purified by recrystallization from ethyl acetate-hexane to give the title compound having the following physical data (5.14 g, yellow powder).

Workup

  1. temperatureunder cooling with ice
  2. temperatureUnder cooling with ice, to this solution
  3. stirringthe mixture was stirred for 1 hour at room temperature
  4. filtrationThe solid that appeared was collected by filtration
  5. dissolutionwas dissolved in ethyl acetate
  6. customwas dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a8c09de2fcaa4c4ba312743a218f82d2
Source dataset
uspto-grants-2007_03
Patent number
US07196198B2

Reaction notes

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