Azobisisobutyronitrile → HCID 22929706, compound

Reaction equation

[Br:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([O:13][CH2:14][CH3:15])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:29]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH2:16][Br:29])=[CH:4][C:5]([O:13][CH2:14][CH3:15])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

Procedure

After dissolving ethyl 5-bromo-2-ethoxy-4-methylbenzoate (19.72 g) in carbon tetrachloride, azobisisobutyronitrile (1.13 g) was added and the mixture was heated to reflux for 30 minutes. N-bromosuccinimide was added and the mixture was further heated to reflux for 1 hour. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (10.54 g) as a colorless oil.