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
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-bromomethyl pyrazole(2.5 g, 7.18 mmol) in DMSO (40 mL) was added copper(I) oxide(2.16 g, 15.08 mmol) and water (12 mL). The reaction mixture was stirred at 60° C. for 2 hours then cooled to RT and stirred at RT overnight. The next day, the mixture was filtered through celite, filter pad was washed with ethyl acetate(20 mL); the filtrate was partitioned between ethyl acetate(50 mL) and water(50 mL); organic phase was separated and washed with water(3×30 mL); dried over sodium sulfate; filtered, concentrated, flash chromatography (ethyl acetate : hexane, 1:6) to afford 1-(3-cyano-4-fluorophenyl)-3-trifluoromethyl-5-hydroxymethyl pyrazole(1.7 g). CI mass spectrum m/z (rel. intensity) 286 (M+H, 100).
Workup
- temperaturethen cooled to RT
- stirringstirred at RT overnight
- filtrationThe next day, the mixture was filtered through celite
- filtrationfilter pad
- washwas washed with ethyl acetate(20 mL)
- customthe filtrate was partitioned between ethyl acetate(50 mL) and water(50 mL)
- customorganic phase was separated
- washwashed with water(3×30 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-db60bfc85dff428f94cba57dd6b8eb3a
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06020357
Reaction notes
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