As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 22385-77-9 name is 1-Bromo-3,5-di-tert-butylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 22385-77-9
Preparation 502-(3,5-Di-tert-butylphenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane Bubble nitrogen through DMF (150 mL) for about 15 min prior to adding the reagents. Then dissolve l-bromo-3,5-di-tert-butylbenzene (20.93 g, 77.74 mmol), bis(pinacolato)diboron (22.70 g, 89.40 mmol), and (Iota, – bis(diphenylphosphino)ferrocene)palladium(II) chloride (3.17 g, 3.89 mmol) in the DMF. Stir for 10 min. Add potassium acetate (22.89 g, 233.23 mmol) and bubble argon through the solution for 7 min. Heat the reaction to 85 ¡ãC with stirring for 24 h. Dilute the reaction with water (1.5 L). Collect the resulting brown precipitate by vacuum filtration and washing with water. Dissolve the residue in dichloromethane. Dry this solution over sodium sulfate, filter; collect the filtrate; and concentrate under reducedpressure. Triturate the resulting solids with hot hexanes (400 mL) and filter, washing with hexanes. Concentrate the filtrate to a volume of approximately 300 mL. Place the solution in a freezer overnight. Collect the solid by vacuum filtration and rinsing with cold hexanes. Concentrate the filtrate under reduced pressure to a volume of 150 mL. Cool this mixture in the freezer for about 1.5 h. Collect the resulting solids by vacuum filtration and rinse with cold hexanes. Combine the 2 crops and dry under high vacuum to afford the title compound (21.85 g, 89percent) as a light tan crystalline solid. XH NMR (400 MHz, CDC13) delta 1.33 (s, 12H), 1.33 (s, 18H), 7.53 (t, J = 2.0 Hz, 1H), 7.65 (d, J = 2.0 Hz, 2H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,5-di-tert-butylbenzene, and friends who are interested can also refer to it.
Reference:
Patent; ELI LILLY AND COMPANY; BLEISCH, Thomas, John; COATES, David, Andrew; HUGHES, Norman, Earle; JONES, Scott, Alan; NORMAN, Bryan, Hurst; WO2013/66640; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary