Category: 54962-75-3

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., Product Details of 54962-75-3

A solution of l-allyl-4-methylpiperazine (2.12 g, 14.0 mmol) and 9-BBN (0.5 M in THF, 1.7 g, 28 mL, 14.0 mmol) was EPO heated at reflux for 3 h and then cooled to RT. The solution was added to a mixture of 3-bromo-5- (trifluoromethyl)aniline (3.Oo g, 12.5 ittmol) , potassium carbonate (8.64 g, 62.5 mmol) , PdCl2(PPh3J2-CH2Cl2 adduct (0.457 g, 0.6 mmol) , DMF (30 mL) and water(2 mL) . The mixtre was heated to 75C for 24. The mixture was concentrated, triturated with dichloromethane, and filtered. The filtrate was concentrated and the residue was purified via column chromatography on silica gel (gradient elution with 0-20% methanol-dichloromethane) to afford 3- (3- (4-methylpiperazin- 1-yl)propyl) -5- (trifluoromethyl)benzenamine as a brown oil. MS m/z = 302 [M+H]+. CaIc’d for C15H22F3N3: 301.

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WO2006/44823; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3, 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. 54962-75-3 name is 3-Bromo-5-(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.

Reference Example 68 1-[3-bromo-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol; 3-Bromo-5-(trifluoromethyl)aniline (5.0 g) and 1,4-dibromobutan-2-ol (4.83 g) were stirred at 100C for 3 hr. After cooling to room temperature, to the reaction mixture was added saturated aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10 – 50:50) to give the title compound (5.6 g, yield 22%) as a brown oil. 1H-NMR (300 MHz, CDCl3)delta:1.66 (br. s, 1 H), 2.08 – 2.27 (m, 2 H), 3.23 – 3.32 (m, 1 H), 3.38 (td, J = 8.8, 3.4 Hz, 1 H), 3.44 – 3.59 (m, 2 H), 4.65 (br. s, 1 H), 6.65 (s, 1 H), 6.80 (t, J = 1.9 Hz, 1 H), 7.02 (s, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2295406; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3,Some common heterocyclic compound, 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 1; Preparation of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I2000 g of 3-bromo-5-trifluoromethylaniline of formula II, 1368 g of 4-methylimidazole of formula III, 181 g of 8-hydroxyquinoline, 238 g of CuI, 666.6 g of NaOH, 933 g of CaO and 7000 ml of DMSO were loaded into a 10 L of 3-neck flask. The reaction mixture was protected with nitrogen and was then stirred at 120 C. 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 45-50 C. and poured into a 50 L reactor. 8.4 L of 14% ammonia was added dropwise and then stirred for 1 hour at 45-50 C. The mixture was cooled down to room temperature. 16.8 L of water and 10 L 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 5 L¡Á3 of 5% of brine for three times. The upper organic layer was separated and dried over 1 kg of anhydrous Na2SO4 overnight. The mixture was filtered and concentrated to obtain 2.3 kg of solid. The residue was dissolved in 2 L of ethyl acetate at 45 C. To the solution was then added 8 L of petroleum ether dropwise at 45 C. The mixture was cooled down slowly to 0-15 C. and stirred for 1 hour. A large amount of precipitate was formed and filtered. The filtered cake was dissolved in 2 L of ethyl acetate at 45 C. The solution was then added 8 L of petroleum ether dropwise at 45 C. The mixture was cooled down slowly to 15-0 C. and stirred for 1 hour. A large precipitate was formed and filtered. The filter cake was dried at 45 C. and 954 g of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 54962-75-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 54962-75-3 as follows.

3-(4-MetIzyI-1H-imidazo1-1-y1)5-(trifluorornethy1)ani1ine: A suspension of 3-bromo-5-(trifluorornethyl)aniline (4.8 g, 20 mmol), 4-methylimidazole (1.97 g, 24 mmol), potassium carbonate (3.04 g, 22 mmol), Cu (0.57 g, 3 mmol), and 8-hydroxyquinoline (0.44 g, 3 mrnol,) in dry DMSO (20 mL) in a pressure tube was degassed by bubbling N2 into the suspension for 10minutes while stirring. The tube was sealed tightly. The mixture was heated at 120 C (oil bath temperature) for 15 h. The mixture was cooled down to 45- 50C and 14% aq. NH4OH (20 mL) was added. The mixture was maintained at this temperature for I h. After cooling to rt, water and ethyl acetate were added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were passed through a short silica gel column to remove most of green/blue Cusalts. The filtrate was dried over sodium sulfate and concentrated on a rotavap. The crude product was recrystallized from EtOAc/hexanes, giving pure pale yellow needles. The motherliquor was concentrated and the residue was purified on silica gel column (5% methanol/methylene chloride), yielding a second crop as pale yellow needles.

According to the analysis of related databases, 54962-75-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; GOZGIT, Joseph, M.; RIVERA, Victor, M.; SHAKESPEARE, William, C.; ZHU, Xiaotian; DALGARNO, David, C.; WO2013/162727; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary