Succinimide → 4'-(Bromomethyl)-2-cyanobiphenyl
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.C1(=O)NC(=O)CC1>N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N.C(Cl)Cl.O>[Br:16][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
A four-necked glass flask equipped with a stirrer and reflux condenser was charged with 180 g of methylene chloride, 63.2 g of 4'-methylbiphenyl-2-carbonitrile, 58.8 g of N-bromosuccinimide and 90 mg of 2,2'-azobis (2,4-dimethylvaleronitrile) and the reaction was conducted under reflux with stirring at an internal temperature of 45°-47° C. for 3 hours. Refluxing was further continued for 1 hour and after cooling to an internal temperature of 35°-38° C., the reaction mixture was treated with 200 g of water twice to transfer the byproduct succinimide into the water layer. The methylene chloride layer was allowed to cool gradually to 0° C., whereupon white crystals separated. The crystals were recovered by filtration, washed with cold methylene chloride and dried to give 71.6 g of 4'-bromomethylbiphenyl-2-carbonitrile. Yield 80.5%.
Workup
- customA four-necked glass flask equipped with a stirrer
- temperaturereflux condenser
- temperatureunder reflux
- temperatureRefluxing
- waitwas further continued for 1 hour
- temperatureafter cooling to an internal temperature of 35°-38° C.
- customseparated
- filtrationThe crystals were recovered by filtration
- washwashed with cold methylene chloride
- customdried
Sources & evidence
- ORD record
- ord-adde99da2fcd4007bab9c8b6f656eb60
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05312958
Reaction notes
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