Synthesis
General procedure for the synthesis of 1-bromo-4-iodonaphthalene from 4-bromo-1-naphthylamine: 1-amino-4-bromonaphthalene (60 g, 0.27 mol) was placed in a single-necked flask and the reaction was carried out under argon protection. Acetonitrile (500 ml) was added as a solvent and the reaction mixture was cooled to 0 °C and kept until 1-amino-4-bromonaphthalene was completely dissolved. Subsequently, boron nitrite (42 g, 49 ml, 0.41 mol) and copper bromide (73 g, 0.32 mol) were added sequentially with continuous stirring for 3 h at room temperature. Upon completion of the reaction, the reaction was terminated by slow addition of 1N HCl aqueous solution (600 ml). The resulting solid product was collected by filtration and washed sequentially with distilled water and ether to remove impurities. Finally, the target compound 1-bromo-4-iodonaphthalene (76 g, 85% yield) was purified by column chromatography.
References
[1] Patent: WO2011/105700, 2011, A1. Location in patent: Page/Page column 23
[2] Patent: US2011/152246, 2011, A1. Location in patent: Page/Page column 121-123
[3] Journal of the Chemical Society, 1885, vol. 47, p. 523
[4] Journal of the Chemical Society, 1895, vol. 67, p. 912
[5] Tetrahedron Letters, 2004, vol. 45, # 42, p. 7883 - 7885
