2270-59-9, name is 5-Bromo-2-methylpent-2-ene, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 2270-59-9
A dry Schlenk tube equipped with a stirring bar was charged with dimethyl oxalate(0.5 g, 4.2 mmol, 1.0 equiv.) and then the flask was evacuated and refilled with N2 (x3). Dry THF (0.7 M) was added and the mixture was cooled to -78 C. A freshlyprepared solution of 4-methylpent-3-en-1-yl)magnesium bromide (1.05 equiv.) wasadded by dropwise [Grignard preparation: a dry Schlenck tube equipped with astirring bar was charged with Mg turnings (1.1 equiv.) and then the flask wasevacuated and refilled with N2 (x 3). The minimum amount of THF was added andthen 5-bromo-2-methylpent-2-ene (0.3 equiv.) was added neat. Once the Grignardreaction started the remaining 5-bromo-2-methylpent-2-ene (0.75 equiv.) were addedas a solution in THF (2 M). The corresponding mixture was stirred for 1 additional hour]. The mixture was allowed to warm to room temperature overnight. NH4Cl was added and the mixture was diluted with Et2O. The layers were separated and the organic layer was dried (MgSO4), filtered and evaporated. Purification by columnchromatography on silica gel, eluting with petrol-Et2O 95:5, gave S7 (0.2 g, 25%) asan oil. 1H NMR (400 MHz, CDCl3) delta 5.07 (1H, t, J = 7.2 Hz), 3.86 (3H, s), 2.87 (2H,t, J = 7.3 Hz), 2.32 (2H, q, J = 7.3 Hz), 1.67 (3H, s), 1.62 (3H, s); 13C NMR (101 MHz, CDCl3) delta 194.1, 161.6, 133.7, 121.9, 53.0, 39.7, 25.8, 21.9, 17.8; HRMS (ESI): Found MNH4+ 188.1280 C9H18O3N requires 188.1281.
Statistics shows that 2270-59-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methylpent-2-ene.
Reference:
Article; Davies, Jacob; Angelini, Lucrezia; Alkhalifah, Mohammed A.; Sanz, Laia Malet; Sheikh, Nadeem S.; Leonori, Daniele; Synthesis; vol. 50; 4; (2018); p. 821 – 830;,
Bromide – Wikipedia,
bromide – Wiktionary