Reaction #87293

Reaction equation

2-(4-chlorobenzylidene)indan-1-one

N-bromosuccinimide

benzoyl peroxide

→

14a

3-Bromo-2-(4-chlorobenzylidene)indan-1-one

Solvents

CCl4

Conditions

Workup

1. 1
   Temperatureunder reflux for one hour
2. 2
   Filtrationfiltered once
3. 3
   OtherThe precipitate was separated

Procedure

2-(4-chlorobenzylidene)indan-1-one (2.44 g, 9.58 mmol) was dissolved in 35 mL of CCl4. N-bromosuccinimide (1.685 g, 9.58 mmol) and benzoyl peroxide (122 mg, 0.52 mmol) were added in one portion. The solution was then stirred under reflux for one hour and then filtered once cooled to room temperature. The precipitate was separated using flash column chromatography (15:1 Hexanes/EtOAc) provided 14a as white crystals.

Source