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

HRID 59015

Reaction equation

HRID 59015 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-814d39fdb22b4d17948eb2814524dcdd
Source dataset
uspto-grants-2016_09
Patent number
US09439877B2

Linked notes

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