Azobisisobutyronitrile → 3-(Bromomethyl)biphenyl
Reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[CH:11][CH:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 3-phenyltoluene (1.80 mL, 10.9 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (2.124 g, 11.93 mmol) and the mixture heated to 70° C. AIBN (50 mg, 0.30 mmol) was added and the mixture refluxed for 30 mins. Additional AIBN was added (50 mg, 0.30 mmol) and the mixture refluxed for 16 hours. The reaction was cooled, filtered, and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 5% EtOAc in hexanes) to afford the title compound as a white solid.
Workup
- temperaturethe mixture refluxed for 30 mins
- temperaturethe mixture refluxed for 16 hours
- temperatureThe reaction was cooled
- filtrationfiltered
- customthe solvent evaporated in vacuo
- customThe residue was chromatographed (Silica gel, 5% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-0bc455fdad6c4568b19c27e59f766821
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080870
Reaction notes
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