Iodine → 2-iodobenzene-1,3-diol

HRID 494842Notes

Reaction equation

HRID 494842 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[I:9]I.C([O-])(O)=O.[Na+]>O>[I:9][C:3]1[C:1]([OH:2])=[CH:8][CH:7]=[CH:6][C:4]=1[OH:5]

Participants

5

Reactant 3

HCID 807IodineHCID 5054ResorcinolHCID 516892Sodium Bicarbonate

Product 1

HCID 6168332-iodobenzene-1,3-diolYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Resorcinol (2.75 g, 25 mmol) in 20 mL of water and ice was treated with iodine (6.7 g, 26.4 mmol) and NaHCO3 (2.3 g, 27.4 mmol) in one portion. After stirring for 1 hour, the precipitate was separated by filtration and the filtrate was extracted twice (2×75 mL) with diethyl ether. The organic phase was dried over sodium sulfate and evaporated under reduced pressure. The solid was triturated with 20 mL of chloroform and left at −18° C. for 24 hours. The solid was separated by filtration to provide the title compound (78% yield). 1HNMR (300 MHz, CDCl3) δ 4.85 (s, 1H), 6.30 (m, 2H), 6.95 (m, 1H). MS (CDI) m/z 237 (M+H)+.

Workup

  1. customthe precipitate was separated by filtration
  2. extractionthe filtrate was extracted twice (2×75 mL) with diethyl ether
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe solid was triturated with 20 mL of chloroform
  6. waitleft at −18° C. for 24 hours
  7. customThe solid was separated by filtration

Sources & evidence

ORD record
ord-cbc1810316af483297cc9ed0be5d987a
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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