Potassium Carbonate → 4-(2-fluoroethyl)-4-phenyl-1H-pyrazole

HRID 1280758Notes

Reaction equation

HRID 1280758 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][F:21].BrC(F)C>O.CS(C)=O>[F:21][CH2:20][CH2:19][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][NH:10][N:9]=[CH:8]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 129822-Fluoroethyl bromideHCID 1391064-PhenylpyrazoleHCID 235106171-Bromo-1-fluoroethane

Product 1

HCID 184260994-(2-fluoroethyl)-4-phenyl-1H-pyrazoleYield 88.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To 2.0 grams of 4-phenyl-1H-pyrazole, 10 mL of dimethyl sulfoxide and 1.5 g of potassium carbonate were added and the solution was stirred at room temperature. Then, 1.5 grams of 1-bromo-2-fluoroethane was added dropwise. After addition of the bromofluoroethane, the mixture was stirred at room temperature for 24 hours, then poured into 100 mL of water. The precipitated product was filtered off, washed with water, and air-dried. There was obtained 2.0 grams of 4-(2-fluoroethyl)-4-phenyl-1H-pyrazole. The compounds summarized in Table 1 were prepared using essentially the same procedure as shown above. Each of the compounds so formed is characterized by its NMR characteristics.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. filtrationThe precipitated product was filtered off
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-e3a1edc734d3407184696e8c2e594993
Source dataset
uspto-grants-2002_09
Patent number
US06451835B1

Reaction notes

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