Potassium Fluoride → 5-fluoro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 1588784Notes

Reaction equation

[F-:1].[K+].[CH3:3][N:4]1[C:8](Cl)=[C:7]([CH:10]=[O:11])[C:6]([C:12]([F:15])([F:14])[F:13])=[N:5]1>CN(C=O)C>[F:1][C:8]1[N:4]([CH3:3])[N:5]=[C:6]([C:12]([F:15])([F:14])[F:13])[C:7]=1[CH:10]=[O:11]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of anhydrous KF (4 g) in anhydrous DMF (20 mL) was stirred under N2 and 1-methyl-3-trifluoromethyl-5-chloropyrazole-4-carboxaldehyde (10.6 g) added. The mixture was heated at 150 ° C. for 6 h. The mixture was poured onto ice (250 g) and was mixed thoroughly. The mixture was extracted with ether (5×50 mL). The ether solution was dried (MgSO4) and concentrated in vacuo leaving an amber liquid (10 g). The liquid was distilled under reduced pressure to give one fraction, 8.0 g yellow liquid b.p. 68-74 ° C. @ 0.4 Torr.

Workup

additionThe mixture was poured onto ice (250 g)
additionwas mixed thoroughly
extractionThe mixture was extracted with ether (5×50 mL)
dry with materialThe ether solution was dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3cd56ad042c14fbd888f76fd6c0b5ed1
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05223526

Reaction notes

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