N-Bromosuccinamide → 4-Bromo-2-butyl-5-methoxy-1-indanone

Beteiligte Stoffe

Reaktionsschritte

A solution of 2-butyl-5-methoxy-1-indanone (1.869 g, 8.56 mmol) in anhydrous dimethylformamide (8.6 mL) was treated with N-bromosuccinamide (1.676 g, 9.42 mmol). The resulting mixture was stirred under a nitrogen atmosphere and at room temperature for 14 hours, and then heated in an oil bath at 50° C. for 4 hours. After cooling to room temperature, the mixture was diluted with EtOAc (100 mL), washed with water (4×50 mL) and brine (50 mL), dried over MgSO4, and evaporated under vacuum to a dark amber oil (2.468 g). The crude product was purified by column chromatography on EM silica gel 60 (230-400 mesh, 620 mL dry, packed under CH2Cl2), using CH2Cl2 as eluting solvent, to afford 4-bromo-2-butyl-5-methoxy-1-indanone (1.267 g, contains approx. 3% of the 6-bromo isomer) as a pale tan solid. Earlier fractions afforded the 6-bromo isomer.

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