Synthesis
Bis(dibenzylideneacetone)palladium (1.7 g, 3 mmol) and tri-tert-butylphosphine (1.2 g, 6 mmol) were added to toluene (200 mL) under argon protection using 4-tert-butylaniline (14.9 g, 100 mmol) and 4-tert-butylbromobenzene (21.2 g, 100 mmol). The mixture was heated to 90 °C, followed by the addition of sodium tert-butoxide (0.6 g, 6 mmol) and continued heating to 110 °C. The reaction was carried out under an argon atmosphere. The reaction mixture was stirred under argon atmosphere for 12 hours. After completion of the reaction, it was cooled to room temperature and separated by addition of water. The organic layer was concentrated to give a solid product which was purified by silica gel column chromatography to give the target product di(4-tert-butylphenyl)amine (20.2 g, 72 mmol) in 72% yield.
References
[1] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 4, p. 1021 - 1027
[2] Patent: CN107286027, 2017, A. Location in patent: Paragraph 0052; 0064; 0065; 0066
[3] Patent: CN107573306, 2018, A. Location in patent: Paragraph 0030; 0038
[4] Patent: CN107573357, 2018, A. Location in patent: Paragraph 0039; 0040
[5] Tetrahedron Letters, 2001, vol. 42, # 27, p. 4421 - 4424
