Reaction #6299

Reaction equation

4-triflyltoluene

N-bromosuccinimide

benzoyl peroxide

→

4-Triflyl-alpha-bromotoluene

Solvents

carbon tetrachloride

carbon tetrachloride

Conditions

Workup

1. 1
   Temperatureat reflux for 20 hours
2. 2
   Otherthe solid byproducts are removed by filtration
3. 3
   ConcentrationThe filtrate is concentrated in vacuo
4. 4
   Otherthe product is purified by recrystallization from benzene

Procedure

A stirred solution of 22.4 g (0.1 mole) of 4-triflyltoluene, 178 g (0.1 mole) of N-bromosuccinimide, and 0.48 g (0.2 mole %) of benzoyl peroxide in carbon tetrachloride is heated at reflux for 20 hours. After cooling to room temperature, the reaction is diluted by the addition of carbon tetrachloride, and the solid byproducts are removed by filtration. The filtrate is concentrated in vacuo, and the product is purified by recrystallization from benzene.

Source