Water → 1-(4-Fluoro-3-cyanophenyl)-3-trifluoromethyl-5-hydroxymethylpyrazole

HRID 376435

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

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06020357

Linked notes

Loading…