Synthesis
The general procedure for the synthesis of 2,7-dibromo-9,10-phenanthrenequinone from phenanthrenequinone is as follows:
Example 1: Synthesis of 6,11-bis(phenoxazin-10-yl)-1,4-diazabenzophenanthrene (Compound 1)
1. 9,10-phenanthrenequinone (10 g) and concentrated sulfuric acid (100 mL) were added to a dry reaction vessel under nitrogen protection.
2. N-bromosuccinimide (18 g) was added to the reaction mixture and the reaction was stirred for 2 hours at room temperature.
3. Upon completion of the reaction, the reaction was quenched by the slow addition of water (50 mL), followed by pouring the mixture into ice water (600 mL).
4. The precipitated solid product was collected by filtration and washed with hot water.
5. The crude product was extracted by refluxing with ethyl acetate (100 mL) and then vacuum dried to give 2,7-dibromo-9,10-phenanthrenequinone as a yellow solid in 73% yield.
References
[1] Chemical Communications, 2014, vol. 50, # 32, p. 4172 - 4174
[2] Patent: US2005/176952, 2005, A1. Location in patent: Page/Page column 5
[3] Patent: CN107400129, 2017, A. Location in patent: Paragraph 0113-0114
[4] Organic Letters, 2012, vol. 14, # 10, p. 2564 - 2567
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 8, p. 1714 - 1720
