反应详情

温度

110 °C

A mixture of the product of Example 60, step B (9.0 g, 40.1 mmol) and cyclohexane-1,3-dione (6.74 g, 60.1 mmol) in 10% H2SO4/acetic acid (100 mL) was heated at 110° C. for 12 h. After cooling to ambient temperature, the reaction mixture was diluted with water, basified by treating with 10 N NaOH and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the crude material which was purified by flash column chromatography (SiO2, 90:10 hexanes/ethyl acetate) to provide 7-bromo-3,4-dihydrodibenzo[b,d]furan-1(2H)-one (6.8 g, 64%) as a pale yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.91 (d, J=8.1 Hz, 1H), 7.65 (d, J=1.5 Hz, 1H), 7.45 (dd, J=8.1, 1.5 Hz, 1H), 3.03 (t, J=6.3 Hz, 2H), 2.61 (t, J=6.3 Hz, 2H), 2.35-2.24 (m, 2H).

1. temperatureAfter cooling to ambient temperature
2. extractionextracted with dichloromethane
3. washThe organic layer was washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto give the crude material which
8. customwas purified by flash column chromatography (SiO2, 90:10 hexanes/ethyl acetate)