Potassium Iodide → HCID 57678424, compound

HRID 491508Notes

Reaction equation

HRID 491508 reaction equation
[CH:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7](N)=[CH:6][C:5]=1[O:13][CH3:14])([CH3:3])[CH3:2].N([O-])=O.[Na+].[I-:19].[K+]>Cl>[I:19][C:7]1[CH:6]=[C:5]([O:13][CH3:14])[C:4]([CH:1]([CH3:3])[CH3:2])=[C:9]([O:10][CH3:11])[CH:8]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 57678438HCID 57678438, compound

Product 1

HCID 57678424HCID 57678424, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 4-Isopropyl-3,5-dimethoxy-phenylamine (1.28 g, 6.56 mmol) in 15% hydrochloric acid (20 mL) at 0° C. was added sodium nitrite (0.54 g, 7.87 mmol-dissolved in 4 mL water) dropwise. After stirring 20 minutes, potassium iodide (1.09 g, 6.56 mmol-dissolved in 4 mL water) was added slowly at 0° C. After stirring at room temperature for 18 hours, the reaction mixture was partitioned between ether and 10% aqueous sodium bisulfite solution. The ether layer was washed with water, dried using anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography eluting with hexane yielded 5-Iodo-2-isopropyl-1,3-dimethoxy-benzene (807 mg, 40%) as a white solid, MS (M+H)=307.

Workup

  1. stirringAfter stirring at room temperature for 18 hours
  2. customthe reaction mixture was partitioned between ether and 10% aqueous sodium bisulfite solution
  3. washThe ether layer was washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by silica gel column chromatography
  8. washeluting with hexane

Sources & evidence

ORD record
ord-d8afb5481684441a8a1891b5813ee4ea
Source dataset
uspto-grants-2009_05
Patent number
US07531547B2

Reaction notes

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