反应详情

To a solution/suspension of 6.7 g of the title compound of Step C dissolved in 95 mL of carbon tetrachloride under N2 was added N-bromosuccinimide (6.53 g) followed by a catalytic amount of benzoyl peroxide. The solution was heated at reflux for 2 h. Another 1.63 g of N-bromosuccinimide and a catalytic amount of benzoyl peroxide were added and the solution was heated at reflux for an hour. After cooling, methylene chloride was added and the organic layer was washed successively with water, then with 0.1 N sodium thiosulfate solution, and then with saturated aqueous NaCl. The combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (3-10% diethyl-ether/methylene chloride as eluent) to afford 3.12 g of the title compound of Step D. 1H NMR (CDCl3): δ 7.5 (m,1H), 7.44 (m,2H), 7.22 (m,1H), 4.60 (d,1H), 4.36 (d,1H), 3.96 (s,3H), 3.47 (s,3H).

1. temperatureThe solution was heated
2. temperatureat reflux for 2 h
3. temperaturethe solution was heated
4. temperatureat reflux for an hour
5. temperatureAfter cooling
6. washthe organic layer was washed successively with water
7. dry with materialThe combined organic extracts were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by flash chromatography (3-10% diethyl-ether/methylene chloride as eluent)