Water → HCID 178519429, compound

HRID 25310

Reaction equation

HRID 25310 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[CH:7]=[CH:6][NH:5][N:4]=1.[Cl:10][C:11]1[CH:18]=[C:17](F)[CH:16]=[CH:15][C:12]=1[CH:13]=[O:14].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:10][C:11]1[CH:18]=[C:17]([C:7]2[C:3]([C:2]([F:9])([F:8])[F:1])=[N:4][NH:5][CH:6]=2)[CH:16]=[CH:15][C:12]=1[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 178519429HCID 178519429, compoundYield 550.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.08 g (30.0 mmol) of 3-trifluoromethylpyrazol, 4.75 mmol (30.0 mmol) of 2-chloro-4-fluorobenzaldehyde and 4.14 g (30.0 mmol) of potassium carbonate in 30 ml of N,N-dimethylformamide were stirred at 60° C. for 2 hours. After cooling to room temperature, the reaction mixture was poured into 100 ml of water, and the organic matters were extracted with 50 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. The residue afforded 7.18 g of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzaldehyde (yield 87.2%) as a pale yellow powder, after washed with n-hexane.

Workup

  1. extractionthe organic matters were extracted with 50 ml of ethyl acetate twice
  2. washwashed with 50 ml of water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-aef1a357148a4a72b8b8de7e3b3f270c
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Linked notes

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