Benzoyl Peroxide → 1-(Bromomethyl)-4-chlorobenzene

HRID 742548Notes

Reaction equation

HRID 742548 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][Br:1])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 78104-ChlorotolueneHCID 11439SuccinimideHCID 67184N-bromobutanimide

Product 1

HCID 693291-(Bromomethyl)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (19 g, 0.107 mole) and benzoyl peroxide (2.5 g, 0.01 mole) were added to p-chlorotoluene (13 g, 0.103 mole) in carbon tetrachloride (100 mL). The reaction mixture was stirred and refluxed gently for 2 hours. When the succinimide rose to the surface, the reaction was finished. The solution was cooled to room temperature and the succinimide was filtered off. The filtrate was evaporated on a rotary evaporator. Then distillation gave p-chlorobenzyl bromide as colorless crystal (80° C.-85° C./1 mm Hg).

Workup

  1. temperaturerefluxed gently for 2 hours
  2. filtrationthe succinimide was filtered off
  3. customThe filtrate was evaporated on a rotary evaporator
  4. distillationThen distillation

Sources & evidence

ORD record
ord-4d33f9951f7d49b5bd1be7bbec5d70b3
Source dataset
uspto-grants-1996_09
Patent number
US05554753

Reaction notes

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