Iodine → 3,5-Dichloro-2-iodophenol

HRID 710301Notes

Reaction equation

HRID 710301 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[I:10]I>O.OO>[Cl:1][C:2]1[C:3]([I:10])=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 807IodineHCID 115713,5-Dichlorophenol

Product 1

HCID 401517703,5-Dichloro-2-iodophenolYield 102.9%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 3,5-dichlorophenol (0.6 g; 3.68 mmol) in H2O (15 ml), 30% H2O2 was added followed by I2 (0.47 g; 1.85 mmol). The resulting mixture was vigorously stirred for 8 h at room temperature, then extracted with CH2Cl2 (15 ml) and the organic phase was dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.55 g; 52%) as colourless solid. 1H-NMR (CDCl3) 5.58 (s, 1H); 6.89 (s, 1H); 7.06 (s, 1H).

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2 (15 ml)
  3. dry with materialthe organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified by FCC (SiO2; CH2Cl2)

Sources & evidence

ORD record
ord-7809765cb7b847408ca6cf7f887fa44b
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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