These common heterocyclic compound, 51554-93-9, name is 1-Bromo-4-octylbenzene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of 1-Bromo-4-octylbenzene
[0056] N-butyl lithium (11.5 mmol, 4.6 mL, 2.5 M in hexanes) was slowly added via syringe to a THF (50 mL) solution of /; – o c t y 1 b ro m o benzene (3.10 g, 11.5 mmol) at -78 C. The reaction was kept at -78 C for 0.5 h. Me2C03(0.33 g, 3.64 mmol, 0.31 mL) was added to the solution via syringe. The solution was then warmed to room temperature. After the solution was stirred overnight, water was added to the solution to quench the reaction. The mixture was extracted three times with Et20, and the organic extracts were combined and washed twice with brine, dried (Na2S04), filtered, and concentrated to dryness. The resulting crude product was purified by flash column chromatography using basic aluminum oxide (activated, basic, Brockmann I, from Aldrich). Gradient elution (hexanes, hexanes/EtOAc in a 50/1 ratio, EtOAc) gave the pure product as a colorless oil, 1.33 g, 58.1% yield.[0057] 1H NMR (400 MHz, C2D2CL d 7.36 – 7.10 (m, 12H), 2.71 – 2.57 (m, 6H), 1.67 (m, 6H), 1.44 – 1.25 (m, 30H), 1.02 – 0.85 (m, 9H).13C NMR (151 MHz, C2D2Cl4) d 144.16, 141.63, 127.68, 127.63, 81.85 (Ar3C, weak signal, confirmed by HMBC experiment), 35.42, 31.77, 31.28, 29.37, 29.32, 29.15, 22.60, 14.14. HR-MS (ESI) Calcd for C43H6(M-OH)+: 579.4930, Found: 579.4946
The synthetic route of 1-Bromo-4-octylbenzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; NORTHWESTERN UNIVERSITY; MARKS, Tobin J.; GAO, Yanshan; LOHR, Tracy L.; CHRISTIANSON, Matthew D.; KLOSIN, Jerzy; CARNAHAN, Edmund M.; YOUNG, Andrew J.; (26 pag.)WO2019/191539; (2019); A1;,
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