55289-36-6, A common compound: 55289-36-6, name is 3-Bromo-2-methylaniline, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
A mixture of 3-bromo-2-methylaniline (4.000g) , 4, 4, 4′, 4′, 5, 5, 5′, 5′-octamethyl-2, 2′-bi (1, 3, 2-dioxaborolane) (6.550g) and potassium acetate (4.220g) in 1, 4-dioxane (44.8mL) and DMSO (9.0mL) was purged with nitrogen for 10 min. [1, 1′-Bis (diphenylphosphino) ferrocene] -dichloropalladium DCM adduct (0.527g) was added, the mixture was purged for another 5min then was heated at reflux for 2h. The mixture was cooled and filtered through Celite. The solids were washed with EtOAc, and the combined filtrates were washed with water and brine, and dried and concentrated. The residue was purified by column chromatography (eluting with hexane-EtOAc using a gradient from 20: 1 to 85: 15) . 2-methyl-3- (4, 4, 5, 5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl) aniline (compound M1) as a light yellow waxy solid (4.400g, 88%) .[0356]1H NMR (400 MHz, chloroform-d) delta 7.21 (1H, dd, J=7.3, 1.0 Hz) , 7.02 (1H, t, J=7.7 Hz) , 6.75 (1H, dd, J=7.8, 1.0 Hz) , 3.54 (2H, br. s. ) , 2.37 (3H, s) , 1.34 (12H, s) . Mass spectrum m/z 233.3, 234.3, 235.3 (M+H)+.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Bromo-2-methylaniline, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; BETTA PHARMACEUTICALS CO., LTD; WANG, Yiqian; FU, Bang; ZHANG, Yao; LIU, Xiangyong; WANG, Jiabing; DING, Lieming; (103 pag.)WO2019/192506; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary