Electric Literature of 2270-59-9, These common heterocyclic compound, 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, its 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.
General procedure: Freshly activated and dried magnesium turnings (1.38 equiv relative to aldehyde) were weighed into a flame-dried round bottom flask equipped with a stir bar. The flask was purged with nitrogen, cooled to 0 C, and diethyl ether dispensed (to approximate concentration 0.6 mmol/mL). Seventy microliters 1,2-dibromoethane were added to activate the magnesium and stirred for 15 minutes. At 0 C, 5-bromo-2-methyl-2-pentene (1.25 equiv relative to aldehyde) was added dropwise to the stirring magnesium turnings and stirred for 2 hours (consumption of magnesium observed). After formation of the Grignard reagent, the necessary aldehyde (freshly distilled to ensure purity), in diethyl ether, was added to the reaction mixture dropwise at 0 C and stirred for 18 hours. The reaction was quenched with concentrated NH4Cl solution dropwise and diluted with DI water and diethyl ether. The organic layer was separated and aqueous layer extracted three times with diethyl ether in a separatory funnel. The combined organics were washed with brine, dried with anhydrous MgSO4, filtered, and concentrated to afford a crude oil, which was taken on to the next step without further purification
The synthetic route of 2270-59-9 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Gesmundo, Nathan J.; Nicewicz, David A.; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 1272 – 1281;,
Bromide – Wikipedia,
bromide – Wiktionary