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2-Bromoanthraquinone 10 (8.50 g, 0.0296 mol, 1 equiv) and a 50:50 mixture of isopropyl alcohol and tetrahydrofuran (200 mL) were stirred for 10 minutes at 0° C., forming a yellow suspension. NaBH4 (6.70 g, 0.177 mol, 6.0 equiv.) was added to the suspension at 0° C. The mixture was stirred at 0° C. for three hours, turning red in color. The solution was then warmed to room temperature. Additional NaBH4 (3.35 g, 0.089 mol, 3.0 equiv.) was added to the solution at room temperature and the solution was stirred at room temperature for 12 hours, turning into an orange suspension. Deionized water (10 mL) was added to the solution at room temperature and the solution was stirred at room temperature for an additional 12 hours. The consumption of 2-bromoanthraquinone 10 was monitored by thin-layer chromatography (35% CHCl3/hexane, Rf=0.33). Once the consumption of 2-bromoanthraquinone 10 stopped entirely (it was never fully consumed), the volatiles were removed by rotary evaporation. 3 M HCl was slowly added to the solution until bubbling ceased, then additional 3 M HCl (30 mL) was added. The solution was heated at reflux for 6 hours, turning into an opaque, yellow suspension in the process. The mixture was cooled to room temperature, turning into a transparent solution containing yellow-brown crystals. As much water as possible was removed by rotary evaporation. The contents were then vacuum-filtered and washed using deionized water to remove any water, acid and ionic salt, leaving behind a yellow-brown colored solid. The vacuum-filtration receiving flask was changed and the solid was washed with CH2Cl2 through the filter paper. The CH2Cl2 was removed through rotary evaporation. The remaining solid was purified by column chromatography (100% hexane, Rf=0.27), providing 2-bromoanthracene 11 as a white, powdery solid (2.00 g, 26%). 1H NMR (CDCl3): δ 8.42 (s, 1H), 8.34 (s, 1H), 8.18 (d, 1H), 8.01 (m, 2H), 7.87 (d, 1H), 7.50 (m, 3H).

1. customforming a yellow suspension
2. stirringThe mixture was stirred at 0° C. for three hours
3. temperatureThe solution was then warmed to room temperature
4. stirringthe solution was stirred at room temperature for 12 hours
5. stirringthe solution was stirred at room temperature for an additional 12 hours
6. customThe consumption of 2-bromoanthraquinone 10
7. customOnce the consumption of 2-bromoanthraquinone 10
8. customwas never fully consumed), the volatiles
9. customwere removed by rotary evaporation
10. addition3 M HCl was slowly added to the solution
11. customuntil bubbling
12. additionadditional 3 M HCl (30 mL) was added
13. temperatureThe solution was heated
14. temperatureat reflux for 6 hours
15. temperatureThe mixture was cooled to room temperature
16. additioncontaining yellow-brown crystals
17. customAs much water as possible was removed by rotary evaporation
18. filtrationThe contents were then vacuum-filtered
19. washwashed
20. customto remove any water, acid and ionic salt
21. customleaving behind a yellow-brown colored solid
22. filtrationThe vacuum-filtration
23. washthe solid was washed with CH2Cl2 through the filter paper
24. customThe CH2Cl2 was removed through rotary evaporation
25. customThe remaining solid was purified by column chromatography (100% hexane, Rf=0.27)