反应详情

温度

0 °C

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.

1. customquenched with 2-propanol (100 mL)
2. customSolvent was removed in vacuo
3. additionThe residue was diluted with water (1 L)
4. extractionextracted with ethyl acetate (2×500 mL)
5. washThe combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationconcentrated