Br[C:2]1([Br:10])[CH:9]2[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][OH:13].[Al]>C1(C)C=CC=CC=1.Cl([O-])(=O)(=O)=O.[Ag+]>[Br:10][C:2]1[CH:3]([CH:12]([OH:13])[C:11]([O:15][CH3:16])=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=13.85 g of silver perchlorate (18.6 mmol) are added to a solution of 8,8-dibromobicyclo[5.1.0]octane 16 (2.5 g, 9.3 mmol) and methyl glycolate (6.35 ml, 83.9 mmol) dissolved in 5 ml of anhydrous toluene in a dry round-bottomed flask under Ar protected from light by an aluminum film. The reaction mixture is stirred at ambient temperature for 1 h 30 and then the silver salts are filtered off through a sintered glass funnel and washed with AcOEt. The solution is concentrated under vacuum to give a viscous brown oil which is purified by chromatography on silica gel (cyclohexane/2-15% AcOEt) to produce 17 in the form of a yellow oil (w=1.7 g, i.e. 66% yield).
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