Reference of 583-75-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 583-75-5 name is 4-Bromo-2-methylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
Step A: ammonium tetrafluoroborate (20.97 g, 200 mmol) was dissolved in aqueous acetic acid (500 ML AcOH/250 ML water) and cooled to 0 C. 2-Methyl-4-bromoaniline (18.61 g, 100 mmol) and 42 ML of aqueous concentrated HCl (36% w/w, 12N, 500 mmol) were sequentially added.The mixture was stirred for 20 minutes at 0 C. and NaNO2 (7.59 g, 110 mmol) was added.The reaction was stirred for 1 hour at 0 C. and warmed to room temperature.After 16 hours at room temperature, the mixture was concentrated under reduced pressure and the residue was azeotroped with toluene and dried under high vacuum.The solid was suspended in 500 ML of CHCl3 and KOAc (12.76 g, 130 mmol) and 18-crown-6 (7.93 g, 30 mmol) were added.The reaction was stirred for 1.5 hours at room temperature.The mixture was washed with water, dried over anhydrous MgSO4, filtered through Celite and concentrated under reduced pressure to provide 30 g of 5-bromo-1H-indazole (compound 2f) as a tan solid.The crude material was used without further purification.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methylaniline, and friends who are interested can also refer to it.
Reference:
Patent; Munson, Mark; Rizzi, James; Rodriguez, Martha; Kim, Ganghyeok; US2004/176325; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary