N-bromobutanimide → Methyl 2-(4-methylsulfonylphenyl)-3-phenylazulene-1-carboxylate

Participants

Reaction Steps

Methyl 3 -bromo-2-(4-methylthiophenyl)azulene-1-carboxylate: To a solution of 2-(4-methylsulfonylphenyl)-1-phenylazulene (2.00 g) in CCl4 (20.0 ml) was added N-bromosuccinimide (1.26 g) and α,α'-azobis(isobutyronitrile) (0.01 g), and the reaction mixture was heated under reflux for 1 hr. The mixture was filtered, and concentrated. The crude product was purified by SiO2 column chromatography (benzene/Et2O, 100:1) to give the title compound (2.40 g) as violet crystals; mp 98°-100° C.

Provenance & Evidence