6-Bromo-1-hexene synthesis
- Product Name:6-Bromo-1-hexene
- CAS Number:2695-47-8
- Molecular formula:C6H11Br
- Molecular Weight:163.06
629-03-8
2695-47-8
General method: To a stirred solution of 1,6-dibromohexane (1 eq.) in anhydrous tetrahydrofuran (THF, 0.1 M) was added potassium tert-butoxide (tert-BuOK, 1.15 eq.) in batches over a period of 30 min under argon protection. The reaction mixture was stirred under reflux conditions for 16 h before being cooled to room temperature and subsequently quenched with deionized water. The resulting mixture was diluted with diethyl ether and the organic and aqueous layers were separated. The aqueous layer was extracted several times with diethyl ether, all organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography with petroleum ether as eluent to obtain the target product 6-bromo-1-hexene. 2.3.1 Synthesis of 6-bromo-1-hexene 6-Bromo-1-hexene was synthesized from 1,6-dibromohexane (8.1 g, 33.6 mmol) according to the general method described above. Yield: 4.3 g (79% yield) as a colorless oil. Thin layer chromatography (TLC) Rf value: 0.71 (100% hexane unfolding, potassium permanganate solution color development). 1H NMR (CDCl3, 500MHz, ppm): δ5.79 (ddt, J = 17.0, 10.2, 6.7Hz, 1H), 5.02 (ddd, J = 17.1, 3.5, 1.6Hz, 1H), 4.97 (ddt, J = 10.2, 2.2, 1.2 Hz, 1H), 3.41 (t, J = 6.8 Hz , 2H), 2.13 - 2.05 (m, 2H), 1.92 - 1.83 (m, 2H), 1.54 (tt, J = 9.3, 6.6 Hz, 2H). 13C NMR (CDCl3, 126MHz, ppm): δ 138.27, 115.14, 33.87, 32.95, 32.29, 27.48.
629-03-8
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2695-47-8
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Yield:2695-47-8 79%
Reaction Conditions:
with potassium tert-butylate in tetrahydrofuran for 16 h;Inert atmosphere;Reflux;
Steps:
2.3 General Procedure for the synthesis of 1-bromo-ω-alkenes
General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product. 2.3.1 6-Bromo-1-hexene 3 The title compound was synthesized from 1,6-dibromohexane (8.1 g, 33.6 mmol) following the above protocol. Yield: 4.3 g (79%), colorless oil. Rf: 0.71 (n-hexane 100%, visualized with KMnO4 solution). 1H NMR (CDCl3, 500 MHz, ppm): δ 5.79 (ddt, J = 17.0, 10.2, 6.7 Hz, 1H), 5.02 (ddd, J = 17.1, 3.5, 1.6 Hz, 1H), 4.97 (ddt, J = 10.2, 2.2, 1.2 Hz, 1H), 3.41 (t, J = 6.8 Hz, 2H), 2.13 - 2.05 (m, 2H), 1.92 - 1.83 (m, 2H), 1.54 (tt, J = 9.3, 6.6 Hz, 2H). 13C NMR (CDCl3, 126 MHz, ppm): δ 138.27, 115.14, 33.87, 32.95, 32.29, 27.48.
References:
Saied, Essa M.;Le, Thuy Linh-Stella;Hornemann;Arenz, Christoph [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 14,p. 4047 - 4057] Location in patent:supporting information
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