Synthesis
The general procedure for the synthesis of 12-bromo-1-dodecatriene from 1,12-dibromododecane is as follows: 1,12-dibromodecane (1 eq.) was dissolved in anhydrous THF (0.1 M) under argon protection with stirring. Potassium tert-butoxide (1.15 eq.) was added in batches over 30 min. The reaction mixture was heated to reflux and stirred for 16 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched with water. The reaction 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 and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel fast column chromatography using petroleum ether as eluent to obtain the target product 12-bromo-1-dodecene.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3382 - 3385
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4047 - 4057
[3] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4304 - 4310
[4] Synthetic Communications, 2003, vol. 33, # 12, p. 2151 - 2159
[5] Journal of the American Chemical Society, 2007, vol. 129, # 16, p. 4892 - 4893
