Azobisisobutyronitrile → Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

HRID 620941

Reaction equation

HRID 620941 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:13][O:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[CH:13][O:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 435882Methyl 3-methoxy-2-o-tolylacrylate

Product 1

HCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

20.6 g of the methyl α-(2-methylphenyl)-β-methoxyacrylate obtained by Method A, 17.65 g of N-bromosuccinimide, 0.2 g of azodiisobutyronitrile and 150 ml of CCl4 are slowly heated to 90° C. This temperature is maintained until all the succinimide is floating on the solvent. Filtration is followed by concentrating, the remaining oil is dissolved in about 5 ml of acetone, and n-hexane is added to bring about crystallization. This gives 27.5 g of colorless crystals of mp 86°-87° C.

Workup

  1. filtrationFiltration
  2. concentrationby concentrating
  3. dissolutionthe remaining oil is dissolved in about 5 ml of acetone
  4. additionn-hexane is added
  5. customcrystallization

Sources & evidence

ORD record
ord-9b8c870e7d334ddbab992dc982eb8816
Source dataset
uspto-grants-1989_04
Patent number
US04822908

Linked notes

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