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Potassium Carbonate → 2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzaldehyde

HRID 2408234
Notes
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Reaction equation

HRID 2408234 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[F:11][C:12]([F:19])([F:18])[C:13]1[CH:17]=[CH:16][NH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([N:15]2[CH:16]=[CH:17][C:13]([C:12]([F:19])([F:18])[F:11])=[N:14]2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 867072242-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzaldehydeYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-4-fluorobenzaldehyde (5.0 g, 31.5 mmol), 3-(trifluoromethyl)-pyrazole (4.28 g, 31.5 mmol) and potassium carbonate (6.53 g, 47.3 mmol) in anhydrous N,N-dimethylformamide (40 mL) was stirred for 2 h at 110° C. The reaction mixture was cooled to 0° C., poured into ice water (500 mL) and stirred for 15 min. The precipitate formed was filtered and dried under reduced pressure to afford the title compound (8.1 g), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringstirred for 15 min
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cafc0bb35846459c968d50771d3107c3
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815772B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes