Reaction #4071

Reaction equation

methyl α-(2-methylphenyl)-β-methoxyacrylate

N-bromosuccinimide

succinimide

→

colorless crystals

Yield 97.3%

Methyl α-(2-bromomethylphenyl)-β-methoxyacrylate

Yield 97.3%

Solvents

CCl4

Conditions

Workup

1. 1
   FiltrationThe mixture is filtered
2. 2
   Otherthe filtrate is evaporated down
3. 3
   workup.DISSOLUTIONthe oil which remains is dissolved in about 5 ml of acetone
4. 4
   Otherbrought to crystallization with n-hexane

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.

Source