51554-93-9, name is 1-Bromo-4-octylbenzene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 51554-93-9
Pd(OAc)2 (0.232 mg, 1.032 mumol), and S-Phos (0.424 mg, 1.032 mumol) were added to a suspension of K2CO3 (35.7 mg, 0.258 mmol), 1-bromo-4-octylbenzene (0.012 ml, 0.052 mmol), 5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-[1,2′-bipyridin]-2-one (20 mg, 0.067 mmol) in acetonitrile/water (1.5:1). The suspension was degassed for 5 minutes and refluxed for 6 h. The reaction mixture was extracted with EtOAc, washed with brine, dried with MgSO4 and filtered. After evaporation of the organic solvent under reduced pressure, the resulting residue was purified by column chromatography over silica gel (100% hexanes to 40/60 hexanes/EtOAc) to provide the title compound as an off-white solid (81% yield). 1H NMR (400 MHz, CDCl3) delta 8.75 (t, J = 1.7 Hz, 1H), 8.00 (d, J = 1.6 Hz, 3H), 7.92 (dd, J = 2.1 Hz, 7.1 Hz, 1H), 7.52 (d, J = 8.3 Hz, 2H), 7.41 (m, 1H), 7.31 (d, J = 8.3 Hz, 2H), 6.71-6.63 (m, 1H), 6.36-6.27 (m, 1H), 2.66 (t, J = 7.8 Hz, 2H), 1.71-1.59 (m, 2H), 1.37-1.22 (m, 8H), 0.88 (t, J = 6.8 Hz, 3H); 13C NMR (101 MHz, CDCl3) delta 162.3, 150.5, 147.0, 143.5, 140.2, 136.3, 136.0, 135.9, 134.1, 129.3, 127.0, 122.1, 121.1, 106.3, 35.7, 31.9, 31.5, 29.5, 29.4, 29.3, 29.2, 22.7, 14.1; HRMS (ESI+) m/z calcd for C24H28N2O [M+Na]+ 383.2094, found 383.2113.
Statistics shows that 51554-93-9 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-4-octylbenzene.
Reference:
Article; Raje, Mithun R.; Knott, Kenneth; Kharel, Yugesh; Bissel, Philippe; Lynch, Kevin R.; Santos, Webster L.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 183 – 194;,
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