Azobisisobutyronitrile → 2-(2,2,2-Trifluoroethoxy)-3-chlorobenzyl bromide

HRID 1740603Notes

Reaction equation

HRID 1740603 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[F:14][C:2]([F:1])([F:13])[CH2:3][O:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:12][Br:22]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 18700110HCID 18700110, compound

Product 1

HCID 187001832-(2,2,2-Trifluoroethoxy)-3-chlorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 2-(2,2,2-trifluoroethoxy)-3-chlorotoluene (2.4 g, 11 mmol) from Step 1 above in CCl4 (40 mL) was added NBS (2.1 g, 11 mmol) and AIBN (1.8 g, 11 mmol). The mixture was refluxed for 8 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using hexanes as eluant. 2-(2,2,2-trifluoroethoxy)-3-chlorobenzyl bromide was obtained as an oil (HPLC retention time=22.3 min (method D)).

Workup

  1. temperatureThe mixture was refluxed for 8 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d840f9389554184bfc6ed73730e0031
Source dataset
uspto-grants-1999_10
Patent number
US05968938

Reaction notes

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