Water → HCID 23075677, compound

HRID 854133Notes

Reaction equation

HRID 854133 reaction equation
[F:1][CH:2]([F:17])[O:3][C:4]1[N:8]([CH:9]([CH3:11])[CH3:10])[N:7]=[C:6]([C:12]([F:15])([F:14])[F:13])[C:5]=1[CH3:16].[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:16][C:5]1[C:6]([C:12]([F:15])([F:14])[F:13])=[N:7][N:8]([CH:9]([CH3:10])[CH3:11])[C:4]=1[O:3][CH:2]([F:1])[F:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 23075699HCID 23075699, compound

Product 1

HCID 23075677HCID 23075677, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 10.3 g (40.0 mmol) of 5-difluoromethoxy-4-methyl-1-iso-propyl-3-trifluoromethyl-1H-pyrazole in 40 ml of carbon tetrachloride were added 7.8 g (44.0 mmol) of N-bromosuccinimide and 0.3 (2.0 mmol) of α,α′-azobisisobutyronitrile, followed by heating and refluxing under stirring. The reaction solution was externally irradiated with a light for 1 hour. After the completion of the reaction was confirmed, the reaction solution was poured into water and extracted with chloroform. The resulting organic layer was washed with water and saline, successively, and then dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel column chromatography to obtain 5.5 g (yield: 40.7%) of 4-bromomethyl-5-difluoromethoxy-1-iso-propyl-3-trifluoromethyl-1H-pyrazole.

Workup

  1. temperatureby heating
  2. temperaturerefluxing
  3. customThe reaction solution was externally irradiated with a light for 1 hour
  4. extractionextracted with chloroform
  5. washThe resulting organic layer was washed with water and saline
  6. dry with materialsuccessively, and then dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-047ca8ddced8445b91c444c055b4d656
Source dataset
uspto-grants-2007_08
Patent number
US07256298B2

Reaction notes

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