Boron tribromide → 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenol

HRID 1440139Notes

Reaction equation

HRID 1440139 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[C:15]([O:21]C)=[CH:14][C:13]=2[F:23])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:23])=[CH:14][C:15]([OH:21])=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:8])[F:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 152785744-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 1357687574-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenolYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.4 g (4 mmole) 4-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 20 mL methylene chloride was chilled to 0° C. Next 5.0 mL of a 1M methylene chloride solution of BBr3 (4.9 mmole) was added slowly over 10 minutes. The solution was allowed to stir overnight at room temperature. The solution was washed two times with water, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was recrystallized from hexane to give 0.7 g (54%) of 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenol as a beige solid, mp 89°-90° C.

Workup

  1. washThe solution was washed two times with water
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-87aac3603bed4f65931cceefe9de60f2
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

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