反应详情

[Bis(trifluoroacetoxy)iodo]benzene (3.78 g, 8.78 mmol) and iodine (1.061 g, 4.18 mmol) were added to a stirred solution of ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate (prepared according to the procedure described in WO 2007/071966) (2.16 g, 8.36 mmol, CAS 10207-26-8) in CHCl3 (50 mL). The resulting solution was stirred at ambient temperature for 90 minutes. The reaction mixture was poured into sodium thiosulfate (100 mL), extracted with DCM (2×100 mL), the organic layer was washed with aqueous sodium thiosulfate (2×80 mL), separated, dried over MgSO4, filtered and evaporated to afford a yellow oil which solidified on standing. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the title compound (2.78 g, 87%) as a white solid.

1. customprepared
2. extractionextracted with DCM (2×100 mL)
3. washthe organic layer was washed with aqueous sodium thiosulfate (2×80 mL)
4. customseparated
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customto afford a yellow oil which
9. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane
10. customPure fractions were evaporated to dryness