Benzoyl Peroxide → HCID 22929911, compound

Reaction equation

[C:1]([C:3]1[C:4]([CH3:19])=[CH:5][C:6]([O:16][CH2:17][CH3:18])=[C:7]([CH:15]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])#[N:2].[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:19][C:4]1[C:3]([C:1]#[N:2])=[CH:15][C:7]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[C:6]([O:16][CH2:17][CH3:18])[CH:5]=1

Participants

Procedure

After dissolving tert-butyl 5-cyano-2-ethoxy-4-methylbenzoate (8.91 g) in carbon tetrachloride, N-bromosuccinimide (6.6 g) and benzoyl peroxide (400 mg) were added and the mixture was heated to reflux for 3 hours. The reaction mixture was filtered and concentrated. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield a mixture of the title compound and tert-butyl 5-cyano-2-ethoxy-4-methylbenzoate (starting material) (8.80 g) as a white solid.