N-bromobutanimide → HCID 21188099, compound

HRID 1383605Notes

Reaction equation

HRID 1383605 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[CH:17]=[C:16]([C:18]#[CH:19])[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14]1.[Br:24]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:24][C:19]#[C:18][C:16]1[C:15]([C:20]([F:23])([F:22])[F:21])=[N:14][N:13]([C:3]2[C:4]([Cl:12])=[CH:5][C:6]([C:8]([F:10])([F:9])[F:11])=[CH:7][C:2]=2[Cl:1])[CH:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21188046HCID 21188046, compound

Product 1

HCID 21188099HCID 21188099, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)4ethynyl-3-trifluoromethylpyrazole (3.1 g) in acetone (25 ml) was added N-bromosuccinimide (1.4 g) and silver nitrate (0. 14 g). Stirring was continued at room temperature for 2 hours. The reaction mixture was evaporated and the residue partitioned between ether and water. The organic layer was separated, dried and evaporated. The residue was purified by column chromatography on silica gel (10 g) eluted with hexane and then dichloromethane: hexane (1:1). Combination and evaporation of appropriate fractions, followed by crystallisation from hexane, gave the title compound as a white solid m.p. 92-94° C.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between ether and water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (10 g)
  7. washeluted with hexane
  8. customCombination and evaporation of appropriate fractions
  9. customfollowed by crystallisation from hexane

Sources & evidence

ORD record
ord-dd84dc100fa546e7a7334675f6436808
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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