Acetic Acid → N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of 5-acetylamino-6-bromoindane (43.0 g, 0.17 mmol) in glacial acetic acid (400 ml) at 50°-55° C. was added dropwise a solution of chromium trioxide (70.0 g, 0.7 mmol) in 50% aqueous acetic acid (400 mL) over a period of 30 min. After further stirring for 15 min, the mixture was cooled to 0° C. and quenched with 2-propanol (100 mL). Solvent was removed in vacuo. The residue was diluted with water (1 L) and extracted with ethyl acetate (2×500 mL). The combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine, dried over anhydrous MgSO4 and concentrated to give 36 g (80%) of the title compound as a light brown solid which was contaminated with about 10% of 5-bromo-6-acetylamino- 1-indanone.

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