Azobisisobutyronitrile → 2-Bromomethyl-4-nitro-1-pentafluoroethyl-benzene

HRID 888107Notes

Reaction equation

HRID 888107 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:37])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:37][CH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:16])([F:17])[C:12]([F:14])([F:15])[F:13]

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 105871021-Pentafluoroethyl-2-methyl-4-nitro-benzene

Product 1

HCID 219593672-Bromomethyl-4-nitro-1-pentafluoroethyl-benzene

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

2-Methyl-4-nitro-1-pentafluoroethyl-benzene (2.55 g) was dissolved in CCl4 (30 ml) and AIBN (164 mg) and NBS (1.96 g) were added. The reaction was heated to reflux and stirred for 24 h. The mix was diluted with CH2Cl2, washed with sat'd NaHCO3, dried over MgSO4 and concentrated to give the compound as an oil which was used without further purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. washwashed with sat'd NaHCO3
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a62e44e8c1a942d5885d2d8dbe43e1fc
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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