Hydrogen Bromide → 5-Iodobenzene-1,3-diol

HRID 1003945

Reaction equation

HRID 1003945 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([I:11])[CH:6]=[C:7]([O:9]C)[CH:8]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]([I:11])[CH:6]=[C:7]([OH:9])[CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 6401791-Iodo-3,5-dimethoxybenzene

Product 1

HCID 6167555-Iodobenzene-1,3-diolYield 99.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,5-Dimethoxyiodobenzene (1.19 g) is dissolved in acetic acid (10 ml), and thereto is added 47% hydrobromic acid (10 ml) at room temperature, and the mixture is refluxed for 15 hours. The reaction mixture is cooled to room temperature, and concentrated to dryness under reduced pressure. The residue is dissolved in ethyl acetate, and the organic layer is washed with water, dried, and concentrated under reduced pressure to give 3,5-dihydroxyiodobenzene (1.06 g).

Workup

  1. temperaturethe mixture is refluxed for 15 hours
  2. concentrationconcentrated to dryness under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-82fa8e9a43cd431faf20c55195195adb
Source dataset
uspto-grants-2000_04
Patent number
US06048842

Linked notes

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