Dimethyl malonate → Dimethyl bromomalonate

Participants

Reaction Steps

p-Toluene sulfonic acid monohydrate (11.0 g, 0.057 mol) and N-bromosuccinimide (1.74 g, 0.009 mol) were slowly added to a stirred solution of dimethyl malonate (5.0 g, 0.037 mol) in CH3CH (30 mL). The resulting mixture was heated at reflux for 2 hours, evaporated and dissolved in dichloromethane. The organic layer was washed with H2O, dried over MgSO4 and concentrated. An analytically pure sample was to obtained by column chromatography on silica gel using a 1:4 mixture of ethylacetate/hexane. Yield: 6.0 g (76.0%).

Provenance & Evidence