Benzoyl Peroxide → 1,3-Dibromo-2-(bromomethyl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[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][CH:5]=[C:4]([Br:8])[C:3]=1[CH2:9][Br:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To the solution of 2,6-dibromotoluene (55.5 g, 222.1 mmol) and NBS (43.5 g, 244.3 mmol) in carbon tetrachloride (300 mL) was added benzoyl peroxide (5.37 g, 22.2 mmol). The reaction mixture was refluxed for 20 h, cooled to room temperature, washed with water (300 mL×3) and brine (300 mL) and dried over anhydrous sodium sulfate. The solution was filtered and evaporated to give 1,3-dibromo-2-bromomethylbenzene as a yellow power (71 g). This material was used for next step without further purification.
Workup
- temperatureThe reaction mixture was refluxed for 20 h
- washwashed with water (300 mL×3) and brine (300 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationThe solution was filtered
- customevaporated
Sources & evidence
- ORD record
- ord-118bf696674346bf91f4652946012bfb
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729078B2
Reaction notes
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