Bromide ion → 1-[4-Chloro-2-fluoro-5-(2-propyn-1-yloxy)phenyl]-3,5-dimethyl-4-nitro-1h-pyrazole

HRID 580259Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[C:12]([CH3:19])=[N:11]1.[Br-].[C:21](=O)([O-])[O-].[K+].[K+].[C:27](#N)[CH3:28]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:21][C:27]#[CH:28])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([N+:16]([O-:18])=[O:17])[C:12]([CH3:19])=[N:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(2-fluoro-4-chloro-5-hydroxyphenyl)-3,5-dimethyl-4-nitropyrazole (28.7 g), propargy bromide (13.1 g), anhydrous potassium carbonate (15.2 g) and acetonitrile (200 ml) was stirred at 60° C. for 2 hours. After cooling, the reaction mixture was filtered through a filter to remove crystalline solid matters and the filtrate was concentrated to a small volume under reduced pressure. The concentrated solution was admixed with toluene and water to form two layers. The toluene layer formed (the extract) was separated, washed with water and then dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (31.2 g) as a pale yellow crystalline solid. Recrystallization of this solid from a mixture of n-hexane/ethyl acetate yielded a white crystalline solid. m.p. 125°-126.5° C.

Workup

temperatureAfter cooling
filtrationthe reaction mixture was filtered through
filtrationa filter
customto remove crystalline solid matters
concentrationthe filtrate was concentrated to a small volume under reduced pressure
customto form two layers
extractionextract)
customwas separated
washwashed with water
dry with materialdried over anhydrous sodium sulfate
customRemoval of the solvent
distillationby distillation in vacuo

Sources & evidence

ORD record: ord-31de493e0b4e4c7f812eb71aa05aef05
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04752326

Reaction notes

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