Water → 4-(bromomethyl)-5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazole
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].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.O>C(Cl)(Cl)(Cl)Cl>[Br:16][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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 11.5 g (50.0 mmol) of 5-difluoromethoxy-1,4-dimethyl-3-trifluoromethyl-1H-pyrazole in 50 ml of carbon tetrachloride were added 9.8 g (55.0 mmol) of N-bromosuccinimide and 0.41 (2.5 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 to obtain 17.8 g (purity: 72.0%, yield: 82.7%) of 4-bromomethyl-5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazole.
Workup
- temperatureby heating
- temperaturerefluxing
- customThe reaction solution was externally irradiated with a light for 1 hour
- extractionextracted with chloroform
- washThe resulting organic layer was washed with water and saline
- dry with materialsuccessively, and then dried over anhydrous magnesium sulfate
- customThe solvent was removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-2ad2b046a4bb4a349ee8daa1c2eb0268
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07256298B2
Reaction notes
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