Azobisisobutyronitrile → methyl (Z)-3-(4-bromomethylphenyl)-2-phenylpropenoate

HRID 2255561Notes

Reaction equation

HRID 2255561 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[C:9](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)\[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CCOCC>[Br:27][CH2:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[C:9](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)\[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 816809Methyl 3-(4-methylphenyl)-2-phenylacrylate

Product 1

HCID 86747178methyl (Z)-3-(4-bromomethylphenyl)-2-phenylpropenoateYield 73.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of the product of Step B (31 mg, 0.123 mmol) in dry CCl4 (1 mL) under N2 were added NBS (20 mg, 0.9 eq) and a catalytic amount of AIBN. The mixture was stirred at reflux under N2 for 1.5 hours. The mixture was cooled to room temperature, diluted with Et2O and filtered to remove the precipitated succinimide. The filtrate was concentrated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with 15:1 hexane/EtOAc to afford 27.4 mg (67%) of the title compound.

Workup

  1. temperatureat reflux under N2 for 1.5 hours
  2. filtrationfiltered
  3. customto remove the precipitated succinimide
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified on a silica gel flash chromatography column
  6. washeluted with 15:1 hexane/EtOAc

Sources & evidence

ORD record
ord-0cd096a1f72b441cb64a7af3f457edd6
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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