4-Chlorophenol → 4-Chloro-2-iodophenol

HRID 572954Notes

Reaction equation

HRID 572954 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[I-:9].[Na+].ClOC(C)(C)C>C(#N)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1

Participants

7

Reactant 3

HCID 46844-ChlorophenolHCID 5238Sodium IodideHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 6202344-Chloro-2-iodophenolYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 40 mmol of 4-chlorophenol and 52 mmol of sodium iodide in 80 mL of acetonitrile and 16 mL of water at room temperature add 52 mmol of tert-butyl hypochlorite dropwise over a period of 30 minutes. Stir the reaction mixture for 3 hours at ambient temperature. Dilute the reaction mixture with 200 mL of ethyl acetate. Wash the resulting organic solution successively with 5% aqueous sodium thiosulfate solution and brine and dry over anhydrous magnesium sulfate. Remove the solvent and then crystallize from hexanes to yield 51% of (P9) as a solid.

Workup

  1. washWash the resulting organic solution successively with 5% aqueous sodium thiosulfate solution and brine
  2. dry with materialdry over anhydrous magnesium sulfate
  3. customRemove the solvent
  4. customcrystallize from hexanes
  5. customto yield 51% of (P9) as a solid

Sources & evidence

ORD record
ord-9ccf82a4daaf4ac3a307cb1a6da2bf0a
Source dataset
uspto-grants-2015_05
Patent number
US09029487B2

Reaction notes

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