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

HRID 2072706Notes

Reaction equation

HRID 2072706 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.C1(=O)NC(=O)CC1>N(C(C)(C)C#N)=NC(C)(C)C#N.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 3

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

Product 1

HCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateYield 97.3%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

20.6 g of the methyl α-(2-methylphenyl)-β-methoxyacrylate obtained as described in Method A, 17.65 g of N-bromosuccinimide, 0.2 g of azobisisobutyronitrile and 150 ml of CCl4 are slowly heated to 90° C. and kept at this temperature until all of the succinimide floats on the solvent. The mixture is filtered, the filtrate is evaporated down, the remaining oil is dissolved in about 5 ml of acetone and the solution is brought to crystallization with n-hexane. 27.5 g of colorless crystals of melting point 86°-87° C. are obtained.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated down
  3. dissolutionthe remaining oil is dissolved in about 5 ml of acetone
  4. customthe solution is brought to crystallization with n-hexane

Sources & evidence

ORD record
ord-25f5611750dd405bbcd59a6e6da485c1
Source dataset
uspto-grants-1990_04
Patent number
US04914128

Reaction notes

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