Synthetic Route of 51554-93-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 51554-93-9 name is 1-Bromo-4-octylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Pd(OAc)2 (0.115 mg, 0.514 mumol), and S-Phos (0.211 mg, 0.514 mumol) were added to a suspension of K2CO3 (17.75 mg, 0.128 mmol), 1-bromo-4-octylbenzene (6.12 mul, 0.026 mmol), tert-butyl 4-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (10 mg, 0.026 mmol), in acetonitrile/water (1.5:1). The suspension was degassed for 5 min and then 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 70/30 hexanes/EtOAc) to provide a yellow oil (93% yield). 1H NMR (500 MHz, CDCl3) delta 7.90 (d, J = 8.3 Hz, 2H), 7.58-7.50 (m, 1H), 7.23 (d, J = 7.6 Hz, 2H), 7.10 (d, J = 7.6 Hz, 1H), 6.57 (d, J = 8.5 Hz, 1H), 3.64-3.55 (m, 8H), 2.67-2.60 (m, 2H), 1.67-1.57 (m, 2H), 1.49 (s, 9H), 1.36-1.24 (m, 8H), 0.87 (t, J = 6.8 Hz, 3H); 13C NMR (126 MHz, CDCl3) delta 158.9, 155.5, 155.0, 143.8, 138.3, 137.3, 128.7, 126.7, 109.9, 105.4, 80.0, 45.2, 35.8, 32.0, 31.5, 29.6, 29.4, 29.3, 28.5, 22.8, 14.2; HRMS (ESI+) m/z calcd for C28H41N3O2 [M+H]+ 452.3199, found 452.3605.The Boc-protected amine was dissolved in 10 mL methanol and HCl (g) was bubbled through the solution for one minute. After evaporation of the methanol, diethyl ether was added and the solid filtered. It was washed with cold diethyl ether to yield the title compound as orange oil (92% yield).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-octylbenzene, and friends who are interested can also refer to it.
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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