In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Bromoindolin-2-one
n-BuLi (2.5M in hexane, 158 mL, 396 mmol) was added dropwise to a stirred and cooled (-40C) suspension of 6-bromoindolin-2-one (21.0 g, 99 mmol) and i-Pr2NH (29.4 mL, 208 mmol) in dry THE (225mL) under Ar. During addition the temperature is maintained below -20C. After complete addition, the temperature was allowed to warm to 0C, then a solution of 1 ,2-dibromoethane (25.6 mL, 297 mmol) in dry THF (25 mL) was added dropwise maintaining a temperature of below 10C. After complete addition, the reaction mixture was stirred at room temperature for 1 8h. The reaction mixture was concentrated to a smaller volume (-75 mL) under reduced pressure.The residue was diluted with EtOAc (200 mL) and brine (100 mL). The biphasic mixture was then stirred vigorously. The pH of the solution was brought to a value of 5 by slowly adding 4M aqueous HCI (-50 mL). The biphasic system was filtered through a glass filter in order to remove the solids which appeard in the bisphasic system. The solids were rinsed with EtOAc (-10 mL), collected and dried on the air to give a first batch of INT-1 as a pale solid (13.99 g, 58.8 mmol, 59.3%).The filtrate layers were separated. The aqueous phase was extracted with EtOAc (2x 100 mL). The combined organic phases were washed with brine (100 mL), dried over Na2SO4 and the solvent was distilled off. The viscous dark-brown residue was stirred with EtOAc (25 mL) for 5 mm at rt. The suspension was then slowly diluted with heptane (75 mL) while stirring which again resulted in solids which were filtered off, rinsed with heptane (10 mL), collected and air-dried to give a second batch of INT-1 (1)as a brown solid (6.04 g, 25.4 mmol, 25.6%).LCMS: calculated for [M+H]: 238/240, found: 238/240, mono-Br isotope pattern observed.
The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GRUeNENTHAL GMBH; NARDI, Antonio; JAKOB, Florian; KONETZKI, Ingo; CRAAN, Tobias; HESSLINGER, Christian; DOODEMAN, Robin; (0 pag.)WO2016/8593; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem