Reaction #4069

Reaction equation

N-bromosuccinimide

methyl phenylacetate

→

title compound

Yield 93.1%

Methyl Bromo-Phenylacetate

Yield 93.1%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperatureto reflux
2. 2
   Temperaturerefluxed for about 12 hours
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated by evaporation under vacuum

Procedure

In this example, a mixture containing 5.93 g of N-bromosuccinimide, 5.0 g of methyl phenylacetate; and a catalytic amount (about 0.1 g) of benzoyl peroxide in 50 ml of carbon tetrachloride was warmed to reflux and then refluxed for about 12 hours. The mixture was then cooled to about 0° C. and filtered. The filtrate was concentrated by evaporation under vacuum affording 7.1 g of the title compound as an oil.

Source