Azobisisobutyronitrile → HCID 66767121, compound

HRID 2195537Notes

Reaction equation

HRID 2195537 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:10]([CH3:19])[N:9]2[CH3:20])=[CH:4][CH:3]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:33]N1C(=O)CCC1=O.CCOC(C)=O>C(Cl)Cl>[Br:33][CH2:19][C:10]1[N:9]([CH3:20])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:12](=[O:13])[C:11]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 66767158HCID 66767158, compound

Product 1

HCID 66767121HCID 66767121, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(4-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (1.2 g, 4.3 mmol) and azobisisobutyronitrile (AIBN) (0.09 g, 0.06 mmol) in DCM is added N-bromosuccinimide (NBS) (0.9 g, 4.3 mmol) in three portions at RT. The resulting reaction mixture is stirred at RT overnight. The mixture is concentrated and the residue is purified by silica gel column chromatography eluting with PE:EtOAc (4:1) to give the product as a white solid (1.3 g, 84% yield). MS (m/z) 357.0 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe mixture is concentrated
  3. customthe residue is purified by silica gel column chromatography
  4. washeluting with PE

Sources & evidence

ORD record
ord-7e48b7c7b3f04d5bbe990ef762ce7186
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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