Azobisisobutyronitrile → Methyl 2-(bromomethyl)-6-cyanobenzoate
Reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:2].[Br:14]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:14][CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[C:4]=1[C:5]([O:7][CH3:8])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of EXAMPLE 6B (2.37 g) in chloroform (30 mL) was added N-bromosuccinimide (2.41 g) and AIBN (4 mg), and the mixture was heated at reflux for 18 hours. After cooling, the solvent was removed, and the concentrate was partitioned between ethyl acetate and water. The extract was washed with brine and concentrated, and the concentrate was purified by flash chromatography on silica gel with 20% ethyl acetate in hexanes.