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

HRID 2395649Notes

Reaction equation

HRID 2395649 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-7ed07448752e4484a9e96a7dfc5987dd
Source dataset
uspto-grants-1996_02
Patent number
US05489571

Reaction notes

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