Benzoyl Peroxide → HCID 67530800, compound

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][CH3:12])[C:7]=1[CH3:13])=[O:5])[CH3:2].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][CH3:12])[C:7]=1[CH2:13][Br:21])=[O:5])[CH3:2]

Participants

Procedure

3-Ethyl-4-methyl-isoxazole-5-carboxylic acid ethyl ester (3.5 g, 19.1 mmol), NBS (3.4 g, 19.1 mmol), and benzoyl peroxide (0.46 g mg, 1.91 mmol) were added to 110 mL of carbon tetrachloride and the mixture was refluxed for 16 h. The mixture was cooled to room temperature and concentrated in vacuo. The crude product was purified by flash chromatography (0-10% EtOAc/hexanes) to give 1.03 g of the title compound. MS: (+) m/z 262.17, 264.14 (M+1, 79Br/81Br).