Chlorine → 4-(Chloromethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole

HRID 854128Notes

Reaction equation

HRID 854128 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[CH3:14].C(=O)([O-])O.[Na+].[Cl:21]Cl>C(Cl)(Cl)(Cl)Cl>[Cl:21][CH2:14][C:5]1[C:6]([C:10]([F:13])([F:12])[F:11])=[N:7][N:8]([CH3:9])[C:4]=1[O:3][CH:2]([F:1])[F:15]

Participants

5

Reactant 3

HCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 230756675-(Difluoromethoxy)-1,4-dimethyl-3-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 230756834-(Chloromethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1.00 g (4.35 mmol) of 5-difluoromethoxy-1,4-dimethyl-3-trifluoromethyl-1H-pyrazole in 10 ml of carbon tetrachloride was added 0.55 g (6.52 mmol) of sodium hydrogen carbonate, followed by heating and refluxing under stirring. The reaction solution was externally irradiated with a light and chlorine gas was introduced in a suitable amount while the amount of the aimed compound formed was confirmed by gas chromatography. After the completion of the reaction, a gas chromatographic analysis was conducted to confirm that 4-chloromethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole was formed in an amount of 61.7%.

Workup

  1. temperatureby heating
  2. temperaturerefluxing

Sources & evidence

ORD record
ord-31b8cdf607ec4c8aa023f9986196e5a4
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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