New downstream synthetic route of 583-70-0

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Related Products of 583-70-0, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 583-70-0 as follows.

According to Scheme 1 Step i: To a solution of 1-bromo-2,4-dimethyl-benzene (20.00 g, 108.07 mmol, 1.00 eq) in THF (100 mL) under N2 atmosphere and cooled to -70C, was added n-BuLi (2.5 M, 45.39 mL, 1.05 eq) dropwise. The reaction mixture was stirred at -70C for 2 hr. Then a solution of 1,4-dioxa-spiro[4.5]decan-8-one (17.72 g, 113.47 mmol, 1.05 eq) in THF (100 mL) was added dropwise at -70C, the reaction mixture was stirred at -70C for 2 hr. The reaction mixture was quenched by water (300 mL) and extracted with EtOAc (200 mLx2). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silicagel (Petroleum ether/EtOAc 10/1 to 5/1). Intermediate 2a (24.00 g, 86.00 mmol, 79.57% yield) was obtained as a light yellow solid. 1H NMR (DMSO-d6; 400MHz) delta 7.31-7.29 (m, 1H), 6.90-6.89 (m, 2H), 4.66 (s, 1H), 3.87 (s, 4H), 2.49 (s, 3H), 2.21 (s, 3H), 2.00-1.94 (m, 4H), 1.79-1.76 (m, 2H), 1.53-1.51 (m, 2H).

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pragma Therapeutics; DUVEY, Guillaume; CELANIRE, Sylvain; (118 pag.)EP3459939; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary