Benzoyl Peroxide → 2-Bromo-5-chlorobenzyl bromide

HRID 1714002Notes

Reaction equation

HRID 1714002 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].C1C(=O)N([Br:17])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][Br:17]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 844762-Bromo-5-chlorotoluene

Product 1

HCID 118465052-Bromo-5-chlorobenzyl bromideYield 45%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-bromo-2-(bromomethyl)-4-chlorobenzene was prepared according to literature precedent (J. Am. Chem. Soc. 2002, 124 (7), 1354): a suspension of 1-bromo-2-methyl-4-chlorobenzene (1 eq), NBS (1 eq) and benzoyl peroxide (0.004 eq) in CCl4 (0.7 M) was heated at reflux for 4 h. The reaction was then filtered whilst hot and the volatiles reduced in vacuo. PE was added, and the resultant precipitate filtered off and dried in vacuo to afford the title compound (45%).

Workup

  1. custom1-bromo-2-(bromomethyl)-4-chlorobenzene was prepared
  2. temperaturewas heated
  3. temperatureat reflux for 4 h
  4. filtrationThe reaction was then filtered whilst hot and the volatiles
  5. additionPE was added
  6. filtrationthe resultant precipitate filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-47a464bac5824b0a916dbf111ebfdf66
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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