Iodine → 2-iodobenzene-1,3-diol

HRID 2267004Notes

Reaction equation

HRID 2267004 reaction equation
C(=O)(O)[O-].[Na+].[C:6]1([OH:13])[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=1.[I:14]I>O>[I:14][C:7]1[C:8]([OH:12])=[CH:9][CH:10]=[CH:11][C:6]=1[OH:13]

Participants

5

Reactant 3

HCID 807IodineHCID 5054ResorcinolHCID 516892Sodium Bicarbonate

Product 1

HCID 6168332-iodobenzene-1,3-diolYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Add sodium bicarbonate (27.9 g, 333 mmol) to a solution of benzene-1,3-diol (33.0 g, 300 mmol), and iodine (81.5 g, 321 mmol) in water (225 mL) chilled to 0° C. and stir. Warm the solution to ambient temperature gradually over 1 hour. Extract with diethyl ether, combine organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield a white solid. Triturate the solid in chloroform (100 mL) chilled to −10° C. After 30 minutes, filter the precipitate, washing with cold chloroform to yield the title compound as a white solid (49.0 g, 69%): 1H NMR (DMSO-d6) δ 6.33 (d, 2H), 6.93 (t, 1H), 10.03 (s, 2H).

Workup

  1. temperatureWarm the solution to ambient temperature gradually over 1 hour
  2. extractionExtract with diethyl ether
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto yield a white solid
  7. customTriturate the solid in chloroform (100 mL)
  8. temperaturechilled to −10° C
  9. filtrationfilter the precipitate
  10. washwashing with cold chloroform

Sources & evidence

ORD record
ord-c9acebf0fa124728b036687d355b1e8e
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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