Chlorosuccinimide → HCID 86725157, compound

Participants

Reaction Steps

To a solution of 7-methyl-3-trimethylsilylbicyclo[4.2.0]octa-1,3,5-triene (48.1 g, 0.25 mol) in MeOH (1000 ml) at 25° C., was added N-chlorosuccinimide (37.1 g, 0.28 mol), followed by lithium bromide (24.1 g, 0.28 mol) and the reaction mixture was allowed to stir at this temperature for 2 hrs. It was then quenched with H2O (200 ml), and concentrated under reduced pressure. The residue was extracted with hexane (200 ml×4), the combined organic extracts were washed with H2O (3×200 ml), dried over MgSO4 and concentrated under reduce pressure to give a pale yellow oil. The oil was purified by column chromatography (silica, hexane) to give the desired product 3-bromo-7-methyl-bicyclo[4.2.0]octa-1,3,5-triene as a colourless oil (42.6 g, GC-MS: M+=196, M−=198, isolated as a mixture of isomers).

Provenance & Evidence