Synthesis
Synthesis Example 2: Synthesis of Compound 8
2-1) Synthesis of 2,6-dibromoanthraquinone
In a 10L flask, 198.2 g (1.5 mol) of tert-butyl nitrite and 279.1 g (1.2 mol) of copper (II) bromide were dissolved in 6000 ml of acetonitrile. After raising the temperature of the reaction system to 65 °C, 119.1 g (0.5 mol) of 2,6-diaminoanthraquinone was slowly added and the addition process lasted for 5 min. After the nitrogen generation stopped, the reaction mixture was cooled to room temperature. Subsequently, 3.6 L of aqueous 2N hydrochloric acid was added to the reaction mixture and stirred until the solid precipitated. The solid product was collected by filtration, washed sequentially with excess water, methanol and acetone, and dried to give 2,6-dibromoanthraquinone (180 g, 98.4% yield).
References
[1] Patent: EP2292604, 2011, A2. Location in patent: Page/Page column 23
[2] Angewandte Chemie - International Edition, 2018,
[3] Angew. Chem., 2018, vol. 130, # 48, p. 15907 - 15911,5
[4] Tetrahedron, 2014, vol. 70, # 2, p. 262 - 269
[5] Tetrahedron, 2017, vol. 73, # 40, p. 5892 - 5899
