Azobisisobutyronitrile → HCID 18536041, compound

HRID 2306227Notes

Reaction equation

HRID 2306227 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH3:13].[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[CH2:13][Br:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18536178HCID 18536178, compound

Product 1

HCID 18536041HCID 18536041, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methanesulfonic acid 4-bromo-3-methylphenyl ester, as described above in Step B, (14.3 g, 53.9 mmol), N-bromosuccinimide (14.4 g, 80.9 mmol), and 2,2′-azobisisobutyronitrile (1.34 g, 8.16 mmol) in CCl4 was heated at 80° C. for 18 hours. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography, eluting with a gradient of hexane—5% to 20% EtOAc, to yield the titled product.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with a gradient of hexane—5% to 20% EtOAc

Sources & evidence

ORD record
ord-31c3f441d8e84cf4bf2ed2b4e671501e
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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