Water → HCID 22934875, compound

HRID 254223Notes

Reaction equation

[F-:1].[K+].Cl[C:4]1[N:8]([CH2:9][CH3:10])[N:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:5]=1[CH:15]=[O:16].O.C(OCC)(=O)C>CS(C)=O>[CH2:9]([N:8]1[C:4]([F:1])=[C:5]([CH:15]=[O:16])[C:6]([C:11]([F:14])([F:13])[F:12])=[N:7]1)[CH3:10]

Participants

Conditions

Temperature: 100 °C

Procedure

34.3 g (591.3 mmoles) of potassium fluoride (a spray-dried product) was added, at room temperature, into a solution of a crude product of 5-chloro-1-ethyl-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde (equivalent to 197.1 mmoles) dissolved in 100 ml of dimethyl sulfoxide. The mixture was stirred at 100° C. for 3 days to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water and extraction with ethyl acetate was conducted. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 11.1 g (yield: 26.8%) of 1-ethyl-5-fluoro-3-trifluoromethyl-1H-pyrazole-4-carboaldehyde.

Workup

customto give rise
customto a reaction
customAfter the completion of the reaction
washThe resulting organic layer was washed with water
dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
distillationThe resulting solution was subjected to reduced pressure distillation
customto remove the solvent
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-9627c725785645a5a192348d6fb62785
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875606B2

Reaction notes

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