Electric Literature of 445-02-3, 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. 445-02-3 name is 4-Bromo-2-(trifluoromethyl)aniline, 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.
To a solution of 4-bromo-2-(trifluoromethyl)aniline (500 mg, 2.083 mmol) in pyridine (10 mL) at -15 C was added (R)-2-(tert-butoxycarbonylamino)-4-methylpentanoic acid (578 mg, 2.5 mmol). The mixture was stirred for 5 mm. To this mixture was added POC13 (0.23 3 mL, 2.5 mmol) dropwise over a period of 5 mm. The reaction mixture was stirred at -15 C for 15 mm and was then warmed to room temperature and stirred for 15 mm. Upon completion of the reaction as determined by TLC, the reaction mixture was concentrated under reduced pressure,quenched with water (10 mL), and the pH adjusted to 3 using 1.5 N aq. HC1 solution. The reaction mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic extracts were washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford (R)-tert-butyl (1 -((4-bromo-2- (trifluoromethyl)phenyl)amino)-4-methyl- 1 -oxopentan-2-yl)carbamate (480 mg, 51%yield) as a brown solid: LCMS (ESI) m/e 453.0 [(M+H), calcd for C18H25BrF3N2O3,453.1]; LC/MS retention time (method C): tR = 2.21 min.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-(trifluoromethyl)aniline, and friends who are interested can also refer to it.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; BRONSON, Joanne J.; DZIERBA, Carolyn Diane; MACOR, John E.; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; WO2015/6100; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary