Category: 2270-59-9

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

Adding some certain compound to certain chemical reactions, such as: 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2270-59-9. 2270-59-9

EXAMPLE 5 2-Methyl-5-nitro-2-pentene 5-Bromo-2-methyl-2-pentene (120 g, 0.736 m) is added dropwise to a solution of sodium nitrate (60.9 g, 0.883 m) in dimethylsulfoxide (700 ml) at room temperature under nitrogen. The mixture is stirred for 1 hour and treated with water (500 ml) and petroleum ether (1 l). The organic layer is dried (Na2 SO4) and evaporated in vacuo to give a pale yellow liquid (80.7 g). This material is purified by column chromatography on silica gel (800 g, petroleum ether) to give 2-methyl-5-nitro-2-pentene as a colorless liquid (45.4 g, 48%). ir (neat) 1550 cm-1; nmr (CDCl3) delta: 1.70 and 1.73 (both 0,6H, (CH3)2 C=C<), 2.5~2.93(m, 2H, CH2 4.35 (t, J=8 Hz, 2H, --CH2 --CH2 --NO2), STR7 Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5-Bromo-2-methylpent-2-ene. Reference:
Patent; Ortho Pharmaceutical Corporation; US4177194; (1979); A;,
Bromide – Wikipedia,
bromide – Wiktionary