Water → 2-Chloro-4-(3-trifluoromethylpyrazolyl) benzonitrile

HRID 1823181Notes

Reaction equation

HRID 1823181 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[C:13]#[N: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[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 18070343-(Trifluoromethyl)pyrazole

Product 1

HCID 1785096022-Chloro-4-(3-trifluoromethylpyrazolyl) benzonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (18.4 mmol) of 3-trifluoromethylpyrazole, 2.9 g (18.4 mmol) of 2-chloro-4-fluorobenzonitrile and 2.8 g (20.2 mmol) of potassium carbonate in 20 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. After washed with n-hexane, the residue afforded 4.6 g of 2-chloro-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 92.0%) as a white powder, which was used in Reference Example 3 as the starting material.

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
  5. washAfter washed with n-hexane

Sources & evidence

ORD record
ord-0fb426574d1b4722a7f917c6352584cb
Source dataset
uspto-grants-2006_05
Patent number
US07037930B2

Reaction notes

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