Methyl Glycolate → Methyl 2-bromocyclooctene-3-glycolate

Participants

Reaction Steps

Added to a solution of 8,8-dibromobicyclo[5.1.0]octane (2.5 g i.e. 9.3 mmol) and methyl glycolate (6.35 ml, i.e. 83.9 mmol) dissolved in 5 ml of anhydrous toluene in a dry round-bottomed flask, under Ar and protected from the light by aluminium foil, are 3.85 g of silver perchlorate (i.e. 18.6 mmol). The reaction is stirred for 1 h 30 min at room temperature, then the silver salts are filtered over a frit and washed with AcOEt. The solution is concentrated under vacuum to give a viscous brown oil which is purified by silica gel chromatography (2-15% AcOEt in cyclohexane) to obtain the product in the form of a yellow oil having a mass m=1.6 g, i.e. 65% yield.

Provenance & Evidence