N-bromobutanimide → HCID 21188138, compound

HRID 1383613Notes

Reaction equation

HRID 1383613 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]([CH3:20])=[N:14]1.[Br:21]N1C(=O)CCC1=O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:21][C:19]#[C:18][C:16]1[C:15]([CH3:20])=[N:14][N:13]([C:3]2[C:4]([Cl:12])=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=2[Cl:1])[CH:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 21188061HCID 21188061, compound

Product 1

HCID 21188138HCID 21188138, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)4-ethynyl-3-methylpyrazole (0.53 g) in acetone (5 ml) was added N-bromosuccinimide (0.295 g) and silver nitrate (0.028 g). Stirring was continued at room temperature for 1 hour. The reaction mixture was evaporated and the residue taken up in ether and washed with 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 dichioromethane: hexane (1:1). Combination and evaporation of appropriate fractions, followed by crystailisation from hexane, gave the title compound as a very pale yellow solid m.p. 86-89° C.

Workup

  1. customThe reaction mixture was evaporated
  2. washwashed with 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

Sources & evidence

ORD record
ord-0092bd9f84674ea0a36e818739e3230c
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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