Methyl Glycolate → Methyl 2-bromocyclooctene-3-glycolate

Participants

Reaction Steps

To a solution of 8,8-dibromobicyclo[5.1.0]octane (2.5 g, i.e. 9.3 mmol) and of methyl glycolate (6.32 mL, i.e. 83.9 mmol) dissolved in 5 mL of anhydrous toluene in a dry round-bottomed flask, under Ar and protected from light by a film of aluminum, are added 3.85 g of silver perchlorate (i.e. 18.6 mmol). The reaction is stirred for 1 hour 30 minutes at room temperature, and the silver salts are then filtered off on a sinter and washed with EtOAc. The solution is concentrated under vacuum to give a viscous brown oil, which is purified by chromatography on silica gel (2-150 EtOAc in cyclohexane) to give the product in the form of a yellow oil of mass m=1.6 g, i.e. 65% yield.

Provenance & Evidence