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

HRID 238459Notes

Reaction equation

HRID 238459 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 NaHCO2, 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 NaHCO2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de09dcfcf01c43daa253618bd250f2a1
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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