Iodine → HCID 22316804, compound

HRID 2086739Notes

Reaction equation

HRID 2086739 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10](=[N:12][OH:13])[CH3:11])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[I-].[K+].II.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:13][N:12]=[C:10]([CH3:11])[C:9]=2[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 807IodineHCID 4875Potassium IodideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 86584960HCID 86584960, compound

Product 1

HCID 22316804HCID 22316804, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 4-(4-bromophenyl)-3-phenyl-3-buten-2-one oxime (2.06 g, 6.52 mmol) and sodium bicarbonate (2.46 g, 29.3 mmol) in a mixture of tetrahydrofuran (30 ml) and water (20 ml) was added a solution of potassium iodide (4.09 g, 24.7 mmol) and iodine (1.98 g, 7.82 mmol) in water (30 ml) at room temperature. Then, the resulting mixture was refluxed for 5 hours in the dark. After cooling down to room temperature, 50 ml of saturated aqueous sodium sulfite was added. The organic layer was separated and the water layer was extracted with ethyl acetate (100 ml×2). The combined organic layers were dried over anhydrous magnesium sulfate and evaporated. The obtained residue was chromatographed on a column of silica gel (120 g) as eluting with ethyl acetate/hexane (1:15) to afford 1.64 g (80%) of the title compound as a pale brown oil.

Workup

  1. temperatureThen, the resulting mixture was refluxed for 5 hours in the dark
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted with ethyl acetate (100 ml×2)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe obtained residue was chromatographed on a column of silica gel (120 g)
  7. washas eluting with ethyl acetate/hexane (1:15)

Sources & evidence

ORD record
ord-3057c78d143447b5b37c6b5a861ad45e
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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