Azobisisobutyronitrile → HCID 66970222, compound

HRID 1360011Notes

Reaction equation

HRID 1360011 reaction equation
[CH3:1][O:2][C:3](=[O:16])/[C:4](/[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH3:15])=[CH:5]/[O:6][CH3:7].CC(N=NC(C#N)(C)C)(C#N)C.[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])/[C:4](/[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH2:15][Br:29])=[CH:5]/[O:6][CH3:7]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11715678HCID 11715678, compound

Product 1

HCID 66970222HCID 66970222, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

9.7 g (40 mmol) of the compound obtained in Step 2 was dissolved in 200 ml of carbon tetrachloride, and 0.7 g (4 mmol) of AIBN and 7.9 g (44 mmol) of N-bromosuccinimide were added thereto. The mixture was refluxed for 5 hours, and cooled to room temperature. The reaction mixture was washed with 50 ml of water twice and 50 ml portions of a brine solution, dried over anhydrous MgSO4, and distilled under a reduced pressure to obtain (E)-methyl-2-(2-bromomethyl-4-chlorophenyl)-3-methoxyacrylate containing a small amount of the starting material as an oil.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. washThe reaction mixture was washed with 50 ml of water twice
  3. dry with material50 ml portions of a brine solution, dried over anhydrous MgSO4
  4. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-30e6b27c9ebf485082ab7f7aba0d1e3f
Source dataset
uspto-grants-2011_02
Patent number
US07879835B2

Reaction notes

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