Water → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH2:15]Br)=[CH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[OH2:21]>CS(C)=O.[Cu-]=O>[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([CH2:15][OH:21])=[CH:13][C:12]([C:17]([F:20])([F:19])[F:18])=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1-(3-cyano-4-fluoro-phenyl)-3-trifluoromethyl-5-bromomethylpyrazole (0.6 g, 1.72 mmol) in DMSO (10 mL) was added copper (I) oxide (0.52 g, 3.62 mmol) and water (3 mL). The reaction was stirred at 60° C. overnight. The next day the reaction mixture was filtered through Celite®. The filtrate was partitioned between ethyl acetate and water. The organic was washed three times with water, brine, dried over sodium sulfate, filtered and concentrated to give 1-(3-cyano-4-fluoro-phenyl)-3-trifluoromethyl-5-hydroxymethyl pyrazole (0.45 g, 92% yield) as pure compound: MS (CI): 286 (M+H)+ (100%).
Workup
- filtrationThe next day the reaction mixture was filtered through Celite®
- customThe filtrate was partitioned between ethyl acetate and water
- washThe organic was washed three times with water, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2380dd04fad1478c872c6e40c4548ed7
- Source dataset
- uspto-grants-2004_05
- Patent number
- US06730689B2
Reaction notes
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