Benzoyl Peroxide → 2-Bromo-4-(bromomethyl)-1,3-dichlorobenzene
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
Product 1
Reagents, catalysts & solvents 1
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.