Azobisisobutyronitrile → Methyl 2-(2-chloro-4-bromomethylphenoxy)-2-phenylacetate

HRID 37227Notes

Reaction equation

HRID 37227 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:19]=[C:18]([CH2:20][Br:21])[CH:17]=[CH:16][C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 19385673Methyl 2-(2-chloro-4-methylphenoxy)-2-phenylacetate

Product 1

HCID 19385604Methyl 2-(2-chloro-4-bromomethylphenoxy)-2-phenylacetateYield 34%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1.70 g (5.86 mmol) of the product from Step A dissolved in 20 mL of CCl4 was added 1.04 g (5.86 mmol) of N-bromosuccinimide and 50 mg (catalytic amount) of AIBN. The reaction mixture was stirred and heated at reflux for 7 hours, then an additional 0.20 g of NBS was added. The reaction was refluxed for 48 hours, then cooled and concentrated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 10% ethyl acetate/hexane to afford 0.730 g (34%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 7 hours
  3. temperatureThe reaction was refluxed for 48 hours
  4. temperaturecooled
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-39d78e80e4e24895bb97d7c257516844
Source dataset
uspto-grants-1995_05
Patent number
US05420133

Reaction notes

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