Azobisisobutyronitrile → HCID 18700114, compound

HRID 2289320Notes

Reaction equation

HRID 2289320 reaction equation
[F:1][C:2]([F:14])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH:3]([F:5])[F:4].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:14])([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][Br:22])[CH:3]([F:4])[F:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2776650alpha,alpha,beta,beta-Tetrafluoro-2-methylphenetole

Product 1

HCID 18700114HCID 18700114, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-(1,1,2,2-tetrafluoroethoxy)toluene (2.5 g, 12.2 mmol) in CCl4 (75 mL) was added NBS (2.1 g, 13 mmol) and AIBN (0.65 g, 3 mmol). The mixture was refluxed for 6 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (75 mL) and water (50 mL). The organic phase was separated, dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using hexanes as eluant to give 2-(1,1,2,2-tetrafluoroethoxy)benzyl bromide as a colorless liquid (TLC Rf =0.7 (hexanes)).

Workup

  1. temperatureThe mixture was refluxed for 6 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between EtOAc (75 mL) and water (50 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by pressurized silica gel column chromatography

Sources & evidence

ORD record
ord-ab0076abff254452b73db0515c85e17e
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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