Azobisisobutyronitrile → 1-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

HRID 535833Notes

Reaction equation

HRID 535833 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27754472-Methyl-5-nitrobenzotrifluoride

Product 1

HCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Into a solution of 1-methyl-4-nitro-2-trifluormethylbenzene (4.1 g, 20 mmol) in carbon tetrachloride (30 mL) were added NBS (5.4 g, 30 mmol) and AIBN (493 mg, 3 mmol). The reaction was refluxed overnight and then partitioned with water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with water, dried over Na2SO4, filtered and concentrated to afford the material that was not purified but used directly in the next step.

Workup

  1. temperatureThe reaction was refluxed overnight
  2. custompartitioned with water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford the material that
  10. customwas not purified

Sources & evidence

ORD record
ord-1e3e9aa2b7f645eb888aa5eb14441c43
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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