Water → 4-Chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

HRID 1440138Notes

Reaction equation

HRID 1440138 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([O:18]C)[C:15]([Cl:20])=[CH:14][C:13]=2[F:21])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([OH:18])[C:15]([Cl:20])=[CH:14][C:13]=2[F:21])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:9])([F:8])[F:10]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide3×HCID 186156481-Methyl-3-(2-fluoro-4-chloro-5-methoxyphenyl)-4-chloro-5-trifluoromethyl-1H-pyrazole

Product 1

HCID 111210244-Chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazoleYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.39 g of 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole was dissolved in 80 ml of anhydrous methylene chloride and then cooled with a dry ice/acetone bath and 0.14 ml of boron tribromide added. After allowing to warm to room temperature, the mixture was treated with an additional 0.28 ml of boron tribromide. Added was an additional 1.0 ml of boron tribromide and stirred at room temperature for 6 hours. After stirring, 30-50 ml of ice cooled water was added and the mixture stirred for 10 minutes. The organic phase was extracted with water, dried with anhydrous magnesium sulfate, filtered and concentrated to give 1.28 g of 4-chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, m.p. 123.0°-126.0° C.

Workup

  1. temperaturecooled with a dry ice/acetone bath
  2. additionAdded
  3. stirringAfter stirring
  4. additionwas added
  5. stirringthe mixture stirred for 10 minutes
  6. extractionThe organic phase was extracted with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-43d93fa907824359883bb3ec634c3c96
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

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