Acetic Acid → 1-Iodo-3,5-dimethoxybenzene

HRID 1003944

Reaction equation

HRID 1003944 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)N.C(O)(=O)C.N([O-])=O.[Na+].[I-:20].[K+]>Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([I:20])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 663013,5-DimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 6401791-Iodo-3,5-dimethoxybenzeneYield 60.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
80 °C

Procedure

3,5-Dimethoxyaniline (1.0 g) is suspended in a mixture of hydrochloric acid (3 ml), acetic acid (2 ml) and water (5 ml), and thereto is added dropwise a solution of sodium nitrite (473 mg) in water (5 ml) under ice-cooling over a period of 15 minutes. Ten minutes thereafter, to the mixture is added a solution of potassium iodide (1.62 g) in water (5 ml), and the mixture is warmed to 80° C., and stirred for one hour. The reaction mixture is extracted with diethyl ether, and the extract is washed with water, dried, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate), and is recrystallized from ethyl acetate/hexane to give 3,5-dimethoxyiodobenzene (1.05 g), m.p. 73-74° C.

Workup

  1. temperaturecooling over a period of 15 minutes
  2. extractionThe reaction mixture is extracted with diethyl ether
  3. washthe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate)
  7. customis recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d1a45238f9a541beaf9ff645f880e057
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Linked notes

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