Iodine → HCID 58542540, compound

HRID 1843086Notes

Reaction equation

HRID 1843086 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:6]([CH3:13])[N:5]=1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[I:37]I>C(#N)C.O.C(OCC)(=O)C>[F:14][CH:2]([F:1])[O:3][C:4]1[C:8]([I:37])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:6]([CH3:13])[N:5]=1

Participants

7

Reactant 3

HCID 807IodineHCID 9869224Ammonium cerium (IV) nitrateHCID 58542532HCID 58542532, compound

Product 1

HCID 58542540HCID 58542540, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 500 mg (2.42 mmol) of methyl 3-(difluoromethoxy)-1-methyl-1H-pyrazole-5-carboxylate in 20 ml of acetonitrile is admixed with 665 mg (1.21 mmol) of ammonium cerium(IV) nitrate and 369 mg (1.45 mmol) of iodine and heated under reflux for three hours and afterstirred at room temperature overnight. The reaction mixture is diluted with water and ethyl acetate, and the organic phase is washed with saturated sodium thiosulphate solution, dried over sodium sulphate, filtered and concentrated by evaporation in vacuo. This gives 750 mg of methyl 3-(difluoromethoxy)-4-iodo-1-methyl-1H-pyrazole-5-carboxylate (93%).

Workup

  1. temperatureheated
  2. washthe organic phase is washed with saturated sodium thiosulphate solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-95cbc3afe4c842f3a7e971626efbd833
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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