Azobisisobutyronitrile → HCID 66767121, compound

HRID 1662021Notes

Reaction equation

HRID 1662021 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-be9278d48ae348a08e0a1cf3f220651b
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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