Azobisisobutyronitrile → 2-(Bromomethyl)-4-(trifluoromethoxy)benzonitrile

HRID 842933Notes

Reaction equation

HRID 842933 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[CH:9]=[C:8]([O:10][C:11]([F:12])([F:13])[F:14])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27755552-Methyl-4-(trifluoromethoxy)benzonitrile

Product 1

HCID 226163012-(Bromomethyl)-4-(trifluoromethoxy)benzonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methyl-4-trifluoromethoxy-benzonitrile 15 (1.3 g, 6.5 mmol) in carbon tetrachloride (25 mL) was added N-bromosuccinimide (1.7 g, 9.7 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield a clear oil (70%). 1H NMR (400 MHz,CDCl3) δ7.73 (d, J=8.4 Hz, 1 H, Ar), 7.41 (s, 1 H, Ar), 7.27 (d, J=8.4 Hz, 19 H, Ar), 4.61 (s, 2 H, CH2).

Workup

  1. temperatureThe reaction mixture was refluxed 6 hrs
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompartitioned between ether and water
  5. dry with materialThe ether layer was dried
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (10% ether/hexanes)

Sources & evidence

ORD record
ord-11e44d8c321a446090ad7cd4e4b73954
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Reaction notes

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