Related Products of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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.
To a stirred solution of 4,5-diphenyl-2-((phenylsulfonyl)methyl)oxazole419 (2.7 g, 0.007 moles, 1.0 equiv) in dry THF (50 mL) was added potassium tert-butoxide (0.97 g, 0.003 mol, 1.2 equiv) under a nitrogen atmosphere at 0-5C and stirred was continued for 30 min. To this solution was added dropwise 8-bromo-1-octene (1.51 g, 0.008 mol, 1.1 equiv). After addition of the bromide, the reaction mixture was allowed to warm to room temperature and then stirred overnight. Water (30 mL) was then added to the reaction mixture followed by extraction with dichloromethane (2 x 25 mL). The organic layers were separated and combined, and the aqueous layer was washed with dichloromethane (2 x 10 mL). All the dichloromethane extracts were combined and dried over anhydrous sodium sulfate. Removal of the drying agent and concentration resulted in a reddish crude residue which was purified by column chromatography (hexane/ethyl acetate, 9:1) to give pure 4,5-diphenyl-2-(1-(phenylsulfonyl)non-8-en-1-yl)oxazole 20 (2.3 g, 66% yield) as athick colorless oil. Rf = 0.44 (hexane/ethyl acetate, 7.5:2.5); FT- IR: 3064, 2932, 2857, 1702, 1447, 1308, 1147, 686 cm-1; 1H NMR (400 MHz, CDCl3): delta 7.78-7.75 (m, 2H), 7.65-7.60 (m, 1H), 7.51-7.46 (m, 6H), 7.37-7.33 (m, 6H), 5.81-5.71 (m, 1H), 4.98-4.89 (m, 2H), 4.50 (dd, J = 10 Hz, 5.2 Hz, 1H), 2.40-2.34 (m, 2H), 2.03-1.98 (m, 2H), 1.40-1.31 (m, 8H) ppm; 13C NMR (175 MHz, CDCl3): delta 154.9, 147.0, 138.9, 137.3, 136.0, 134.0, 131.8, 129.1, 129.0, 128.9, 128.7, 128.5, 128.4, 128.2, 127.9, 126.6, 114.3, 65.9, 33.6, 28.8, 28.64, 28.58, 26.9, 26.4 ppm; HRMS calcd for C30H31NO3S (EI+) 485.2025, Found 485.2025
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.
Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Tetrahedron Letters; vol. 58; 13; (2017); p. 1280 – 1282;,
Bromide – Wikipedia,
bromide – Wiktionary