New downstream synthetic route of 2,6-Dibromotoluene

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 69321-60-4.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 69321-60-4, name is 2,6-Dibromotoluene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H6Br2

n-BuLi in hexanes (2.5 M; 8.1 mL, 20 mmol) was added dropwise to a solution of 1,3-dibromo-2-methylbenzene (4.8 g, 19 mmol) in THF (50 mL) at -78 C. at such a rate as to keep the internal reaction temperature below -60 C. After stirring for 30 minutes, tert-butyl (R)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (5.01 g, 21.1 mmol) was added in portions, and the reaction was stirred for a further 30 minutes before being allowed to warm to 0 C. over 2 hours. Aqueous citric acid (1N; 40 mL) was added at 0 C., and the mixture was stirred for 15 min before it was extracted with EtOAc (2*100 mL). The combined organic layers were concentrated under reduced pressure. The residue was stirred in HCl in dioxane (4N; 30 mL) at room temperature for 1 hour and then concentrated. The resulting residue was dissolved in water (100 mL) and extracted with diethyl ether (2*60 mL). The aqueous layer was then basified by addition of Na2CO3 and extracted with DCM (3*100 mL). The combined DCM extracts were dried over Na2SO4, filtered and concentrated to dryness. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Product fractions were concentrated to dryness to afford (R)-1-(3-bromo-2-methylphenyl)propan-2-amine (2.6 g, 60%) as a brown oil. 1H NMR (500 MHz, DMSO-d6, 27 C.) 1.1 (3H, d) 2.34 (3H, s) 2.64 (1H, dd) 2.77 (1H, dd) 3.08 (1H, ddd) 7.05 (1H, t) 7.15 (1H, d) 7.45 (1H, d). NH2 was not observed. m/z: ES+ [M+H]+ 228.

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 69321-60-4.

Reference:
Patent; AstraZeneca AB; YANG, Bin; VARNES, Jeffrey Gilbert; SCOTT, James Stewart; MOSS, Thomas Andrew; O’DONOVAN, Daniel Hillebrand; NISSINK, Johannes Wilhelmus Maria; HUGHES, Samantha Jayne; BARLAAM, Bernard Christophe; (83 pag.)US2017/305909; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary