2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine

white solid powder

2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine serves as a reactant in the synthesis of 2,4-diphenyl-6-(4'-triphenylsilanyl-biphenyl-4-yl)-1,3,5-triazine (DTBT) via coupling with 4-phenylboronic acid triphenylsilane, using tetrakis(triphenylphosphine)palladium(0) and potassium carbonate in toluene under nitrogen at 110 °C[6].

The compound, 2-chloro-4,6-diphenyl-1,3,5-triazine (50 g, 187 mmol) was dissolved in THF (1 L) under a nitrogen environment, (4-bromophenyl)boronic acid (45 g, 224.12 mmol, Aldrich Corporation), and tetrakis(triphenylphosphine)palladium (2.1 g, 1.87 mmol) were added thereto, and the mixture was stirred. Potassium carbonate saturated in water (64 g, 467 mmol) was added thereto, and the obtained mixture was heated and refluxed at 80° C. for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and then, filtered after removing moisture with anhydrous MgSO4 and concentrated under a reduced pressure. This obtained residue was separated and purified through flash column chromatography to obtain 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (70 g and 96%).

[1] Patent: US2017/331067,  2017,  A1. Location in patent: Paragraph 0260-0263
[2] Chemistry - An Asian Journal,  2016,  vol. 11,  # 6,  p. 868 - 873
[3] Patent: KR2015/75169,  2015,  A. Location in patent: Paragraph 0206-0209
[4] Patent: KR2015/59395,  2015,  A. Location in patent: Paragraph 0162; 0163; 0164; 0165
[5] Patent: KR2015/88163,  2015,  A. Location in patent: Paragraph 0342-0345
[6] Kang, J.-W., Lee, D.-S., Park, H.-D., Park, Y.-S., Kim, J. W., Jeong, W.-I., Yoo, K.-M., Go, K., Kim, S.-H., & Kim, J.-J. (2007). Silane- and triazine-containing hole and exciton blocking material for high-efficiency phosphorescent organic light emitting diodes. Journal of Materials Chemistry, 17(35), 3714. https://doi.org/10.1039/b705741e