Iodine → 1-Methyl-3-pentafluoroethyl-4-iodo-1H-pyrazole-5-carboxylic acid

HRID 1843079Notes

Reaction equation

HRID 1843079 reaction equation
[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[I:23]I.[CH3:25][N:26]1[C:30]([C:31]([OH:33])=[O:32])=[CH:29][C:28]([C:34]([F:40])([F:39])[C:35]([F:38])([F:37])[F:36])=[N:27]1.ClCCl>C(#N)C>[CH3:25][N:26]1[C:30]([C:31]([OH:33])=[O:32])=[C:29]([I:23])[C:28]([C:34]([F:39])([F:40])[C:35]([F:37])([F:36])[F:38])=[N:27]1

Participants

6

Reactant 4

HCID 807IodineHCID 6344DichloromethaneHCID 9869224Ammonium cerium (IV) nitrateHCID 148368761-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 462200201-Methyl-3-pentafluoroethyl-4-iodo-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.34 g (2.46 mmol) of ammonium cerium(IV) nitrate and then 0.75 g (2.95 mmol) of iodine are added to a solution of 1.20 g (4.91 mmol) of 1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid in 4.3 ml of acetonitrile and the reaction mixture is heated under reflux for 18 hours. After adding 20 ml of dichloromethane, washing is carried out firstly with water, with sodium disulphite solution and finally with saturated sodium chloride solution. The organic phase is dried over sodium sulphate and the solvent is distilled off at reduced pressure on a rotary evaporator. This gives 1.28 g of 4-iodo-1-methyl-3-pentafluoroethyl-1H-pyrazole-5-carboxylic acid (47%) as an oil.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 18 hours
  3. washwashing
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. distillationthe solvent is distilled off at reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-b1a1585e6c8a4c8eb2f4ea7920ba0066
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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