Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., name: 3-Bromo-5-(trifluoromethyl)aniline
Example 1: Preparation of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I 2000g of 3-bromo-5- trifluoromethylaniline of formula II, 1368g of 4-methylimidazole of formula III , 181 g of 8-hydroxyquinoline, 238g of CuI, 666.6g of NaOH, 933g of CaO and 7000ml of DMSO were loaded into a lOL of 3-neck flask. The reaction mixture was protected with nitrogen and was then stirred at 120C for 69 hours while monitoring for the consumption of 3-bromo-5- trifluoromethyaniline by HPLC. Heating was stopped when 3-bromo-5- trifluoromethyaniline / 4-methylimidazole is not more than 5%. The reaction mixture was cooled down to 45-50C and poured into a 50L reactor. 8.4L of 14% ammonia was added dropwise and then stirred for 1hour at 45-50C. The mixture was cooled down to room temperature.16.8L of water and 10L of ethyl acetate were added to the extract. The upper organic layer was separated and filtered through the filter aid. The lower aqueous layer was washed with 7.5L of ethyl acetate and combined with the above filtrate. The combined organic layer was washed with 5Lx3 of 5% of brine for three times. The upper organic layer was separated and dried over 1kg of anhydrous Na2S04 overnight. The mixture was filtered and concentrated to obtain 2.3kg of solid. The residue was dissolved in 2L of ethyl acetate at 45C. To the solution was then added 8L of petroleum ether dropwise at 45C. The mixture was cooled down slowly to 0-15C and stirred for 1hour. A large amount of precipitate was formed and filtered. The filtered cake was dissolved in 2L of ethyl acetate at 45C. The solution was then added 8L of petroleum ether dropwise at 45C. The mixture was cooled down slowly to 15-0C and stirred for 1hour. A large precipitate was formed and filtered. The filter cake was dried at 45C and 954g of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-l-yl)-benzeneamine of formula I were obtained. (Yield: 47.5%). The obtained compound of formula I had purity of 99.7% on area by HPLC and contained 0.13% on area by HPLC, of the 5 methyl isomer impurity.
The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Teva Pharmaceutical Industries Ltd.; EP2305667; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary