反应详情

温度

0 °C

A solution of 4.14. g of 6-demethyl-6-deoxytetracycline, prepared by the described literature procedure, and 1.99 g of N-bromosuccinimide dissolved in 50 ml of concentrated sulfuric acid is stirred at 0° C. for 45 minutes or until solution occurs. The reaction mixture is added dropwise to 2 L of cold diethyl ether. The resulting precipitate is collected and dried. The solid is dissolved in 2-methoxyethanol, triturated with methanol, collected, washed with methanol and diethyl ether and dried to give 6.22 g of crude product. The solid is recrystallized from 2-methoxyethanol and methanol to give 3.1 g of pure product. MS(FAB): m/z 493 (M+H). 1H NMR(CD3SOCD3): δ 4.3(s, lH, 4-H), 6.8(d, lH, 9-H) and 7.75(d, IH, 8-H).

1. customThe resulting precipitate is collected
2. customdried
3. dissolutionThe solid is dissolved in 2-methoxyethanol
4. customtriturated with methanol
5. customcollected
6. washwashed with methanol and diethyl ether
7. customdried
8. customto give 6.22 g of crude product
9. customThe solid is recrystallized from 2-methoxyethanol and methanol