Water → HCID 21188075, compound

HRID 1383581Notes

Reaction equation

HRID 1383581 reaction equation
[C:1]([C:3]1[C:7]([C:8]#[CH:9])=[CH:6][N:5]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][C:11]=2[Cl:21])[N:4]=1)#[N:2].[Br:22]N1C(=O)CCC1=O.CCOCC.O>CC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[Br:22][C:9]#[C:8][C:7]1[C:3]([C:1]#[N:2])=[N:4][N:5]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([C:17]([F:20])([F:18])[F:19])=[CH:12][C:11]=2[Cl:21])[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 67184N-bromobutanimideHCID 15858752HCID 15858752, compound

Product 1

HCID 21188075HCID 21188075, compound

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethynylpyrazole (100 mg, the compound of Example C5) in acetone (5 ml) was added N-bromosuccinimide (54.9 mg) and silver nitrate (5 mg). Stirring was continued at room temperature for 60 minutes. The reaction mixture was then poured into ether (10 ml) and water (10 ml). The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with dichloromethane: hexane (2: 1) to provide the title compound as a white solid m.p. 166-8° C.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with dichloromethane: hexane (2: 1)

Sources & evidence

ORD record
ord-bcb9c407406b4978a409a1ab6b72934b
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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