Benzoyl Peroxide → 3-Bromo-2-(4-chlorobenzylidene)indan-1-one

HRID 2275315Notes

Reaction equation

HRID 2275315 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[O:16])=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:16])[C:7]1=[CH:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3672172-(p-Chlorobenzylidene)-1-indanone

Product 1

HCID 687485823-Bromo-2-(4-chlorobenzylidene)indan-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

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.

Workup

  1. temperatureunder reflux for one hour
  2. filtrationfiltered once
  3. customThe precipitate was separated

Sources & evidence

ORD record
ord-9f27e8e37682432ba62089a352d77d1e
Source dataset
uspto-grants-2015_09
Patent number
US09127016B2

Reaction notes

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