Dimethyl Sulfoxide → 1-(2-Fluoro-4-chloro-5-isopropyloxyphenyl)-3,4,5-trimethylpyrazole

HRID 580260Notes

Reaction equation

HRID 580260 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[N:11]1.[CH:18](I)([CH3:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C1(C)C=CC=CC=1.O>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:18]([CH3:20])[CH3:19])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[N:11]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 137982331-(2-Fluoro-4-chloro-5-hydroxyphenyl)-3,4,5-trimethylpyrazole

Product 1

HCID 137982341-(2-Fluoro-4-chloro-5-isopropyloxyphenyl)-3,4,5-trimethylpyrazoleYield 104.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2-fluoro-4-chloro-5-hydroxyphenyl)-3,4,5-trimethylpyrazole (25.5 g), isopropyl iodide (18.7 g), anhydrous potassium carbonate (14.5 g) and dimethylsulfoxide (200 ml) was stirred at 80° C. for one hour. After cooling, the reaction mixture was admixed with water and toluene to form two layers. The toluene layer formed was separated, washed with water and then dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (31.1 g) as a pale yellow oil, which was then purified through silica gel column chromatography to yield a colorless oil. nD23 =1.5406.

Workup

  1. temperatureAfter cooling
  2. customto form two layers
  3. customwas separated
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-aa3f665aeac6449994ce1f8b31222b34
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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