Potassium Iodide → 2-Iodo-1,3-diisopropylbenzene

HRID 1756768Notes

Reaction equation

HRID 1756768 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1N)([CH3:3])[CH3:2].N([O-])=O.[Na+].[I-:18].[K+]>O.Cl>[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[I:18])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 32484DiisopropylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 99259602-Iodo-1,3-diisopropylbenzeneYield 44.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

To a solution of 7.09 g (40 mmol) of 2, 6-diisopropylaniline in 54 ml of water and 18 ml of conc. hydrochloric acid was dropwise added a solution of 2.76 g (40 mmol) of sodium nitrite in 16 ml of water with sufficient stirring and ice cooling, and the resultant mixture was stirred for further 10 minutes. A solution of 6.64 g (40 mmol) of potassium iodide in 6 ml of water was added to the mixture, and the mixture was stirred for 4 hours at room temperature and refluxed with heating for 1 hour. After cooling, the reaction mixture was extracted with hexane, and the extract was washed with aqueous sodium nitrite and saturated saline in this order, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with hexane to give 5.09 g of 2, 6-diisopropylphenyl iodide as an oil.

Workup

  1. stirringthe mixture was stirred for 4 hours at room temperature
  2. temperaturerefluxed
  3. temperaturewith heating for 1 hour
  4. temperatureAfter cooling
  5. extractionthe reaction mixture was extracted with hexane
  6. washthe extract was washed with aqueous sodium nitrite and saturated saline in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent evaporated
  9. customThe residue was chromatographed on a silica gel column
  10. washeluting with hexane

Sources & evidence

ORD record
ord-c507b86929da433e80b90c0111087cc2
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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