With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13391-28-1,5-Methoxybenzofuran,as a common compound, the synthetic route is as follows.
To a stirred solution of EtONa (154 kg) in DMF (989 kg) was added EtSH (68.6 kg) at an inner temperature ?35 under nitrogen protection. The mixture was stirred for 6090min at the inner temperature ?35. 5-Methoxybenzofuran (58.75 kg) in DMF (55.0 kg) was added. The mixture was heated to 110-130, stirred for 45hrs, and then concentrated under vacuum below 90. After the mixture was cooled to 1020, 2N HCl (1326 kg) was added dropwise, followed by addition of EtOAc (531 kg) and H2O2(129 kg) at the inner temperature ?35. The mixture was stirred for 3060min. After separation of the organic layer, the aqueous phase was extracted with EtOAc. The combined organic phase was washed with saturated brine twice, and then the solvent was evaporated to dryness. MeOH and a solution of NaOH (44.5 kg) in water (185 kg) were added dropwise into the residue below 40. The mixture was stirred for 5-7 hrs at 3040. Active carbon (74 kg) wet up with water (77 kg) was added. The mixture was stirred for 4-6 hrs at 3040 and filtered and the filter cake was washed with MeOH and water. DCM was charged into the filtrate and pH was adjusted to 1 with 35aq. HCl below 40. The aqueous phase was extracted with DCM, and the organic phase was washed with 25NaCl and concentrated below 40 . The residue was used in the next step directly.1H NMR (400 MHz, DMSO-d6) delta 9.14 (s, 1H) , 7.86 (d, J 2.0 Hz, 1H) , 7.36 (d, J 8.8 Hz, 1H) , 6.94 (d, J 2.4 Hz, 1H) , 6.79 (dd, J 2.0, 0.9 Hz, 1H) , 6.74 (dd, J 8.8, 2.4 Hz, 1H) ppm. MS: M/e 135 (M+1)+.
13391-28-1, As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.
Reference£º
Patent; BEIGENE, LTD.; ZHANG, Guoliang; ZHOU, Changyou; (86 pag.)WO2016/165626; (2016); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem