Electric Literature of 2695-48-9, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2695-48-9, name is 8-Bromo-1-octene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
(Step 1) Anhydrous tetrahydrofuran (10 ml) was added to (4S,5R)-3,4-dimethyl-1-(5,5,6,6,7,7,8,8,8-nonafluoro-octanoyl) -5-phenylimidazolidin-2-one (1.20 g, 2.5 mmol) under nitrogen atmosphere, and the resulting mixture was cooled to -78 C. Lithium bis(trimethylsilyl)amide (2.75 ml, 1.0 M in tetrahydrofuran, 2.75 mmol) was added to the mixture, which was then stirred for 1 hour. After addition of 8-bromo-1-octene (714 mg, 3.0 mmol) and HMPA (1.25 ml) at -78 C., the reaction mixture was warmed with stirring up to -50 C. over 2 hours and up to 0 C. over 30 minutes, and then stirred for 12 hours at 0 C. The reaction mixture was quenched with saturated aqueous ammonium chloride at 0 C., and then extracted with a mixed solvent of ethyl acetate and n-hexane (3:7). The organic layer was washed sequentially with saturated aqueous potassium bisulfate, saturated aqueous sodium chloride, saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure using an evaporator and the resulting residue was purified by silica gel column chromatography (Kanto Kagaku, silica gel 60 (spherical, neutral), 40-100 mum, eluent: ethyl acetate/n-hexane=1/5 3/7) to give (4S,5R)-3,4-dimethyl-1-[(2R)-2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-9-decenoyl]-5-phenylimidazolidin-2-one (1.37 g, Yield 93%). Optical purity: 95.5% de, as measured by HPLC (column: Daicel Chiralpack AD, phi0.46*25 cm, solvent: n-hexane/isopropanol=97/3, flow rate: 0.5 ml/min, detection wavelength: 206 nm) 1H-NMR (270 MHz, CDCl3): delta 7.32-7.13 (m, 5H), 5.87-5.72 (m, 1H), 5.34 (d, J=8.9 Hz, 1H), 5.02-4.91 (m, 2H), 4.10-3.86 (m, 2H), 2.84 (s, 3H), 2.19-1.08 (m, 16H), 0.82 (d, J=6.5 Hz, 3H).
The synthetic route of 8-Bromo-1-octene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Jo, JaeChon; Kwon, HeeAn; Lim, HyunSuk; Choi, JaeYoung; Morikawa, Kazumi; Kanbe, Yoshitake; Nishimoto, Masahiro; Kim, MyungHwa; Nishimura, Yoshikazu; US2003/114524; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary