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

HRID 3975

Reaction equation

HRID 3975 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, and the oil which remains is dissolved in about 5 ml of acetone and 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 oil which remains is dissolved in about 5 ml of acetone
  4. custombrought to crystallization with n-hexane

Sources & evidence

ORD record
ord-f360e909fa154e73a99b18eae08d738d
Source dataset
uspto-grants-1988_02
Patent number
US04723034

Linked notes

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