Sodium Iodide → 1,4-Benzodioxin

HRID 1270424Notes

Reaction equation

HRID 1270424 reaction equation
Br[CH:2]1[O:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4][CH:3]1Br.[I-].[Na+]>CC(C)=O>[O:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[O:7][CH:2]=[CH:3]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 123986892,3-Dibromo-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 1360711,4-Benzodioxin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

73.45 mmol of the compound obtained in Step A above are dissolved in 125 ml of acetone; the solution is then stirred for 2 hours under reflux, in the presence of sodium iodide (359.9 mmol). After evaporating off the solvent, the residue is dissolved in a mixture of water/ethyl acetate (100 ml/200 ml). The organic phase is then washed with 20% aqueous sodium thiosulphate solution and then the aqueous phase is extracted twice with ethyl acetate. The organic phases are combined, dried over magnesium sulphate and then concentrated to dryness. Purification by chromatography over silica gel (petroleum ether/ethyl acetate: 95/5) allows the expected product to be obtained.

Workup

  1. customAfter evaporating off the solvent
  2. dissolutionthe residue is dissolved in a mixture of water/ethyl acetate (100 ml/200 ml)
  3. washThe organic phase is then washed with 20% aqueous sodium thiosulphate solution
  4. extractionthe aqueous phase is extracted twice with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness
  7. customPurification by chromatography over silica gel (petroleum ether/ethyl acetate: 95/5)
  8. customto be obtained

Sources & evidence

ORD record
ord-24817b0c12f94929b546dbb40aa7b874
Source dataset
uspto-grants-2007_04
Patent number
US07202255B2

Reaction notes

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