2,3,6,7,10,11-hexabromobenzo[9,10]phenanthrene

Synthesis

Bromine (9.0 mL, 349 mmol) was added dropwise to a solution of 9,10-benzophenanthrene (3.95 g, 17.3 mmol) and iron powder (410 mg, 7.34 mmol) in nitrobenzene (200 mL) under nitrogen protection with stirring at room temperature for 20 min, and the reaction was subsequently heated up to 210°C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the product was precipitated by the addition of ether (Et2O). The precipitate was collected by filtration and washed thoroughly with ether, acetone and chloroform (CHCl3) sequentially to afford the white powdery product 2,3,6,7,10,11-hexabromobenzo[9,10]phenanthrene (11.5 g, 16.4 mmol, 94.8% yield). The melting point of the product was above 300°C; 1H NMR (300 MHz, CDCl3): δ = 8.72 (s, 6H, Ar-H); IR (KBr): νmax = 1585, 1551, 1454, 1365, 1119, 873, 863 cm-1.

References

[1] Journal of the American Chemical Society, 2017, vol. 139, # 48, p. 17229 - 17232
[2] Tetrahedron, 2015, vol. 71, # 29, p. 4714 - 4721
[3] Journal of Materials Chemistry, 2000, vol. 10, # 7, p. 1519 - 1525
[4] Journal of the American Chemical Society, 2017, vol. 139, # 46, p. 16759 - 16767
[5] Inorganic Chemistry, 2014, vol. 53, # 18, p. 9876 - 9896