反应详情

A solution of 7-amino-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (243 mg, 0.845 mmol) in trifluoroacetic acid (1.7 mL) was treated with 2,3,5,6-tetrabromo-4-methyl-4-nitro-2,5-cyclohexadien-1-one (396 mg, 0.845 mmol). The resulting mixture was placed under a N2 atmosphere, sonicated briefly, and stirred at room temperature for 3 hours. The mixture was diluted with EtOAc (50 mL), washed successively with water, 5% NaHCO3 and brine, dried over MgSO4, filtered, and evaporated under vacuum to a brown oil (659 mg). The crude product was purified by flash chromatography on a Biotage 40S KP-Sil column, eluting with 10:1 hexanes-EtOAc. The product containing fractions were evaporated under vacuum to an orange gum (113 mg, 40%) which was lyophilized from benzene to provide 7-amino-9a-butyl-6-fluoro-4-methyl-8-nitro-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

1. customsonicated briefly
2. washwashed successively with water, 5% NaHCO3 and brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated under vacuum to a brown oil (659 mg)
6. customThe crude product was purified by flash chromatography on a Biotage 40S KP-Sil column
7. washeluting with 10:1 hexanes-EtOAc
8. additionThe product containing fractions
9. customwere evaporated under vacuum to an orange gum (113 mg, 40%) which