Allyl bromide → 1-(2-Fluoro-4-chloro-5-allyloxyphenyl)-3,4,5-trimethylpyrazole

HRID 580261Notes

Reaction equation

HRID 580261 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.[CH2:18](Br)[CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH2:20][CH:19]=[CH2:18])=[CH:4][C:3]=1[N:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[N:11]1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 137982331-(2-Fluoro-4-chloro-5-hydroxyphenyl)-3,4,5-trimethylpyrazole

Product 1

HCID 137982731-(2-Fluoro-4-chloro-5-allyloxyphenyl)-3,4,5-trimethylpyrazoleYield 97.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-fluoro-4-chloro-5-hydroxyphenyl)-3,4,5-trimethylpyrazole (25.5 g), allyl bromide (13.3 g), anhydrous potassium carbonate (14.5 g) and acetonitrile (150 ml) was heated under reflux, with stirring for 3 hours. After cooling, the reaction mixture was filtered through a filter to remove the inorganic salts therefrom and the filtrate was concentrated to a small volume under reduced pressure, affording the titled compound (28.7 g) as a pale brown crystalline solid. Recrystallization of this solid from cyclohexane yielded a white crystalline solid. m.p. 97°-99° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through
  5. filtrationa filter
  6. customto remove the inorganic salts
  7. concentrationthe filtrate was concentrated to a small volume under reduced pressure

Sources & evidence

ORD record
ord-1d1d2e107bcd4aa8bc568ea5c96b3a86
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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