Benzoyl Peroxide → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 378164

Reaction equation

HRID 378164 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:28]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH3:9])[CH:3]=1)[CH2:8][Br:28]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneYield 27.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 5-bromo-m-xylene (24.03 g, 0.13 mole) in benzene (125 mL) was added benzoylperoxide (3.04 g, 0.013 mole). The reaction mixture was heated to reflux in a 250 mL round bottom flask. N-bromosuccinimide (18.15 g, 0.10 mole) was added in portions over 15 minutes. After 2 hours, heating was discontinued and the reaction mixture was allowed to cool to room temperature. Precipitated solids were removed by filtration and the filtrate was concentrated. The residue was taken up in hexane and additional solids were removed by filtration. The filtrate was passed through a small pad of silica gel and the filtrate was concentrated. The resultant yellow oil was titurated with MeOH over ice to give 3-bromo-5-methylbenzyl bromide (7.34 g) as a white solid. MS and NMR were consistent with the desired structure.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux in a 250 mL round bottom flask
  3. temperatureheating
  4. customPrecipitated solids
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customadditional solids were removed by filtration
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7be91d5fc2a145b7b63c46ddf403018b
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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