Benzoyl Peroxide → 2-Bromo-4-(bromomethyl)-1,3-dichlorobenzene

HRID 2235212Notes

Reaction equation

HRID 2235212 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[Cl:10].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:36])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([Cl:8])=[C:6]([CH2:9][Br:36])[CH:5]=[CH:4][C:3]=1[Cl:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27355572-Bromo-1,3-dichloro-4-methylbenzene

Product 1

HCID 592994582-Bromo-4-(bromomethyl)-1,3-dichlorobenzeneYield 65.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Place 2-bromo-1,3-dichloro-4-methylbenzene (50 g, 208 mmol) in carbon tetrachloride (400 mL). Add benzoyl peroxide (5 g, 20.8 mmol) and NBS (38.9 g, 219 mmol) and heat to 80° C. and stir for 16 hours. Cool reaction and filter. Dissolve in hexanes and wash with sodium bisulfate and then with sodium bicarbonate. Purify by distillation. Collect product at 135° C. under reduced pressure to give 43.5 g (65%) of 2-bromo-4-(bromomethyl)-1,3-dichlorobenzene.

Workup

  1. temperatureCool
  2. customreaction
  3. filtrationfilter
  4. dissolutionDissolve in hexanes
  5. washwash with sodium bisulfate
  6. distillationPurify by distillation

Sources & evidence

ORD record
ord-f6ff7763dc5f4bd8ab38da4f8cb58ba8
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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