N-bromobutanimide → HCID 67548259, compound

Reaction equation

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

Participants

Procedure

To 7-fluoro-8-methyl-2-(methyloxy)quinoxaline (50 g, 260 mmol) in dry chloroform (1 L) were added N-bromosuccinimide (52 g, 292 mmol) and benzoyl peroxide (70%, 0.42 g) and the mixture was heated under reflux, illuminated with a 120 W lamp, for 2 h. After cooling, the mixture was washed with water. The aqueous phase was re-extracted twice with dichloromethane and the combined organic fractions were washed with water, dried and evaporated to give product (72.1 g, 100%).