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
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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
821-41-0
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2695-47-8
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2695-47-8
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109-64-8
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1730-25-2
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2695-47-8
297 suppliers
$14.00/5g