Réaction #1517

Équation de réaction

p-toluylic acid

N-bromosuccinimide

→

4-bromomethylbenzoic acid

Rendement 65.3%

Solvants

carbon tetrachloride

Conditions de réaction

Traitement

1. 1
   Autrea reaction
2. 2
   Températureunder reflux for 2 hours
3. 3
   AutreAfter completion of the reaction
4. 4
   Températurethe reaction mixture was cooled in ice bath
5. 5
   FiltrationThe deposited crystalline product was collected by filtration, which
6. 6
   Lavagewas then washed with hexane and water
7. 7
   Autreby drying
8. 8
   AutreThe resultant crystalline product was recrystallized from ethanol
9. 9
   Autreto obtain

Mode opératoire

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