Synthetic Route of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a suspension of 2-bromo-5-methylaniline (9.76 g, 52.5 mmol) in 8 mL of water was added 8.8 mL of concentrated HCl. The reaction mixture was cooled in an ice/NaCl bath (approximately -5 to -10 C). Approximately 8 g of ice was added to the reaction mixture. A solution of NaNO2 (3.60 g, 52.3 mmol) in 16.2 mL of water was added slowly over 40 minutes. The solution was then stirred for an additional 30 minutes with cooling. Separately, a solution of potassium ethyl xanthogenate (10.1 g, 63.0 mmol) in 54 mL of water was prepared and heated to 60 C. The cold solution of diazonium salt was then added slowly over 20 minutes to the solution of potassium ethyl xanthogenate. The reaction mixture was stirred for an additional 30 minutes at 60 C, and then cooled to ambient temperature. It was then poured into a saturated aqueous NaHCO3 solution and extracted three times with dichloromethane. The combined organic extracts were washed with saturated brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. To this residue was added a solution of 1.8 M KOH/EtOH, and the reaction mixture was heated to reflux for 18 hours. The reaction mixture was then cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in water and extracted with diethyl ether. The aqueous phase was then acidified with concentrated HCl and extracted three times with dichloromethane. The combined organic extracts were dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography using 0-5% ethyl acetate/hexanes as eluent to provide 8.26 g (78%) of the title Compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3( ^ ggd: 2.25-2.28 (m, 3H) 3.96 (s, 1H) 6.81 (d, J=8.03 Hz, 1H) 7.18 (d, J=1.89 Hz, 1H) 7.40 (d, J=8.20 Hz, 1H).
The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; FMC CORPORATION; XU, Ming; DEANGELIS, Andrew Jon; LAHM, George Philip; (190 pag.)WO2020/18610; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary