Reaction #1517

Reaction equation

p-toluylic acid

N-bromosuccinimide

→

4-bromomethylbenzoic acid

Yield 65.3%

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Othera reaction
2. 2
   Temperatureunder reflux for 2 hours
3. 3
   OtherAfter completion of the reaction
4. 4
   Temperaturethe reaction mixture was cooled in ice bath
5. 5
   FiltrationThe deposited crystalline product was collected by filtration, which
6. 6
   Washwas then washed with hexane and water
7. 7
   Otherby drying
8. 8
   OtherThe resultant crystalline product was recrystallized from ethanol
9. 9
   Otherto obtain

Procedure

39.7 g (287 mmol) of p-toluylic acid, 51.2 g (287 mmol) of N-bromosuccinimide and 2.8 g (11.5 mmol) of dibenzoyl peroxide were suspended in 350 ml of carbon tetrachloride. Then, the resultant mixture was heated with vigorously stirring to perform a reaction under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled in ice bath. The deposited crystalline product was collected by filtration, which was then washed with hexane and water, followed by drying. The resultant crystalline product was recrystallized from ethanol to obtain 40.3 g of 4-bromomethylbenzoic acid as a white needle crystal (isolated yield: 65%).

Source