Synthesis
Example 1.13.1 Synthesis of 4'-bromo-N,N-diphenyl-[1,1'-biphenyl]-4-amine (35): (4-(diphenylamino)phenyl)boronic acid (1.5 g, 5.19 mmol), 4-iodo-1-bromobenzene (1.33 g, 4.71 mmol), Na2CO3 (1.78 g, 16.8 mmol) and Pd(PPh3 )4 (0.163 g, 0.141 mmol) were dissolved in THF/H2O (28 mL/17 mL) mixed solvent. The reaction mixture was degassed and heated to reflux under argon protection overnight. After completion of the reaction, it was cooled to room temperature and the mixture was poured into dichloromethane (150 mL) and washed sequentially with water (2 x 150 mL) and brine (100 mL). The organic phase was dried with Na2SO4, filtered and purified by fast column chromatography (silica gel, hexane/ethyl acetate 50:1), and finally recrystallized in a solvent mixture of dichloromethane/methanol to give a white solid product (compound 35) (1.64 g, 87% yield).
References
[1] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9435 - 9451
[2] Patent: US2010/326526, 2010, A1
[3] Patent: WO2011/8560, 2011, A1. Location in patent: Page/Page column 47-48
[4] RSC Advances, 2015, vol. 5, # 41, p. 32298 - 32306
[5] Patent: US9172051, 2015, B2. Location in patent: Page/Page column 67; 68; 69; 70; 71; 72; 75; 76
