Azobisisobutyronitrile → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 1771601Notes

Reaction equation

HRID 1771601 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.C1C(=O)N([Br:17])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][Br:17])[CH:3]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Product 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 1-bromo-3,5-dimethyl-benzene (1.0 g, 5.4 mmol, 1.0 eq), NBS (1.06 g, 5.94 mmol, 1.1 mmol) and AIBN (180 mg, 1.08 mmol, 0.2 eq) in CCl4 (20 mL) was stirred at reflux overnight. The reaction was then diluted with water and extracted with CH2Cl2. The organic extracts were combined and washed with aqueous NaHCO3, dried (Na2SO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (Petroleum ether:EtOAc, 1:0 to 10:1) to give the title compound as a light yellow oil (1.2 g, 84%).

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with CH2Cl2
  3. washwashed with aqueous NaHCO3
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by flash chromatography (Petroleum ether:EtOAc, 1:0 to 10:1)

Sources & evidence

ORD record
ord-ee9664107b2843aab8ab3b6624835418
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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