[Br:1][C:2]1[C:3]([O:14][CH3:15])=[C:4]([C:9]([CH2:12]Br)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:16]12[CH:22]([SH:23])[CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH:19]12[CH:22]([S:23][CH2:12][C:9]3[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:14][CH3:15])[C:2]([Br:1])=[CH:11][CH:10]=3)[CH:16]([CH2:21][CH2:20]1)[CH2:17][CH2:18]2A mixture of methyl 3-bromo-6-bromomethyl-2-methoxybenzoate (Intermediate 89, 0.338 g), bicyclo[2.2.1]heptane-7-thiol (Intermediate 183, 0.148 g) and potassium carbonate (0.345 g) in THF (5 ml) was stirred and heated at 60° C. for 3 days. After cooling, the mixture was partitioned between ethyl acetate and water and the organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-10% to give methyl 6-(bicyclo[2.2.1]hept-7-ylthiomethyl)-3-bromo-2-methoxybenzoate (0.244 g).
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