Water → 7-amino-8-bromo-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

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Reaction Steps

A solution of 7-amino-9a-butyl-6-fluoro4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.138 g, 0.481 mmol) in anhydrous N,N-dimethylformamide (4.8 mL) was cooled in an ice bath, placed under a nitrogen atmosphere, treated with N-bromosuccinimide (0.94 g, 0.53 mmol), and stirred at room temperature for 30 minutes. The reaction mixture was poured into a water solution of 10% K2CO3 and extracted with EtOAc. The organic layer was washed with water and evaporated under vacuum. The crude product was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate, developing with 20% EtOAc in hexanes, to afford 7-amino-8-bromo-9a-butyl-6-fluoro-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.089 g, 50%) as a yellow solid.

Provenance & Evidence