Azobisisobutyronitrile → 3-(Bromomethyl)benzophenone

HRID 1890629

Reaction equation

HRID 1890629 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 695113-Methylbenzophenone

Product 1

HCID 895863-(Bromomethyl)benzophenoneYield 77%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

Commercially available 3-methylbenzophenone (4.00 g, 20.4 mmol) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (4.71 g, 26.5 mmol) and 2,2′-azobisisobutyronitrile (1.00 g, 6.09 mmol) was added to the solution, followed by stirring at 75° C. for 6.5 hours. After the reaction mixture was cooled, the precipitates were filterd out. The filtrate was combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 3-bromomethylbenzophenone (4.31 g, yield 77%).

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20)

Sources & evidence

ORD record
ord-b75a6751a95049cb8d4a6eba42d81a6e
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Linked notes

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