Category: 268733-18-2

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. 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: 268733-18-2

General procedure: 4-Bromo-3,5-bis-(trifluoromethyl)aniline (616 mg, 2 mmol, 1 equiv), potassium carbonate (829 mg, 6 mmol, 3 equiv), Pd(PPh3)4 (231 mg, 0.2 mmol, 0.1 equiv), DMF (5 mL, 0.4 M) and (MeO)3B (0.28 mL, 2 mmol, 1 equiv) were added to a flask and the contents heated to 110 C overnight. The reaction solution was filtered using silica gel, Celite, and sea sand. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (1:5 EtOAc:Hex), to give 4-methyl-3,5-bis(trifluoromethyl)aniline (760 mg, 67%). 1H NMR (300 MHz, DMSO-d6): delta 2.42 (s, 3H), 3.88 (s, 2H), 7.09 (s, 2H). This aniline was used for general procedure A (EtOAc:Hex 1:20 ? 1:10) (630 mg, 51%). Slightly brown solid. Mp 192-193 C. 1H NMR (300 MHz, DMSO-d6): delta 2.49 (s, 3H), 7.02 (d, J = 8.8 Hz, 1H), 7.47 (dd, J1 = 8.8 Hz, J2 = 2.7 Hz, 1H), 7.87 (d, J = 2.6, 1H), 8.41 (s, 2H), 10.75 (s, 1H), 11.48 (s, br, 1H). HRMS (APCI), m/z calcd for C16H10ClF6NO2-H: 396.0226, found 396.0238.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Lee, Ill-Young; Gruber, Todd D.; Samuels, Amanda; Yun, Minhan; Nam, Bora; Kang, Minseo; Crowley, Kathryn; Winterroth, Benjamin; Boshoff, Helena I.; Barry III, Clifton E.; Bioorganic and Medicinal Chemistry; vol. 21; 1; (2013); p. 114 – 126;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 268733-18-2, These common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, its 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.

General procedure: Phosphorus trichloride (0.13ml, 1.5mmol) was added to a stirred solution of 3,5-bis(trifluoromethyl)aniline (0.47ml, 3mmol), a catalytic amount of pyridine and 5-chloro salicylic acid (621.3mg, 3.6mmol) in anhydrous toluene (10ml) in in a Radley?s Carousel reaction tube under an argon atmosphere. After the reaction mixture was refluxed for overnight, it was cooled to room temperature and aq. sodium bicarbonate was added dropwise until PH=6 – 7. After extracting with ethyl acetate, the organic layers was dried, dried (MgSO4) and concentrated in vacuo. After chromatography (EA-Hex, 1:10) of the crude product, and followed by recrystalization from EtOAc/hexane provided 2a as a white solid (320mg, 28%).

The synthetic route of 268733-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kang, Sunghyun; Min, Hye-Jin; Kang, Min-Seo; Jung, Myung-Geun; Kim, Semi; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1748 – 1751;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 268733-18-2, 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. 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Disodium phosphate 18.2 g (123 mmol) and tetrabutylammonium hydrogen sulfate 2.1 g (6.20 mmol) were dissolved in a 500 mL solution of acetone and dichloromethane, followed by the addition of 4-bromo-3,5-bis-trifluoromethyl aniline 10.0 g (32.5 mmol) dropwise with a oxone and the reaction solution was stirred for 1 hour at 0 C. Potassium hydroxide was added to maintain the acidity of the reaction solution between 7.5 and 8.5. After completion of the reaction, the solution was diluted with dichloromethane and washed with distilled water several times to remove salts. Magnesium sulfate was then added to the dichloromethane solution and the solvent was filtered then evaporated and the resulting reactant was passed through a silica column pale to give a light yellow compound, 1-bromo-4-nitro-2,6-bis(trifluoromethyl)benzene (8.05 g, 23.8 mmol 73.3% yield). [0103] Melting point: 56-57 C. [0104] 1H NMR (CDCl3, 400 MHz, ppm): 8.71 (s, 2H). [0105] 13C NMR (DMSO-d6, 100 MHz, ppm): 146.62, 132.48 (q, J=31.9 Hz), 126.71 (q, J=5.7 Hz), 125.63, 121.68 (q, J=272.9 Hz).

The synthetic route of 4-Bromo-3,5-bis(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kim, Sang Youl; Kim, Sun Dal; Chung, Im Sik; US2015/45481; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 268733-18-2, 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. 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) 1.2 g of 4-bromo-3,5-bis(trifluoromethyl)aniline was dissolved in 10 mL of toluene, and 500 mg of 2-pyridine carboxyaldehyde and then a catalytic amount of pyridinium p-toluenesulfonate were added and reacted at about 100C overnight, and then the reaction solution was left to cool. To the reaction solution, 180 mg of sodium borohydride and 10 mL of ethanol were added and reacted at room temperature for about one hour. Then, water and ammonium chloride were added in proper amounts, followed by stirring. A crude product obtained by extraction with ethyl acetate was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/3) to obtain 1.08 g of N-(4-bromo-3,5-bis(trifluoromethyl)phenyl)-2-pyridine methanamine (compound No. II-19).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-3,5-bis(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2172456; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 268733-18-2, A common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, molecular formula is C8H4BrF6N, its 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.

(1)1.0 g of 3,5-bis(trifluoromethyl)-4-bromoaniline was dissolved in 3 mL of hexamethylphosphoric acid triamide, and 730 mg of copper cyanide was added and reacted at 140C for 8 hours under irradiation with microwaves. The reaction solution was left to cool, and then, to the reaction solution, water and ethyl acetate were added, whereupon an insoluble solid content was removed by filtration through cerite. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were put together and washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/2) to obtain 550 mg of 3,5-bis(trifluoromethyl)-4-cyanoaniline as white solid.

The synthetic route of 268733-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2172456; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 268733-18-2, These common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, its 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.

(1) 300 mg of 4-bromo-3,5-bis(trifluoromethyl)aniline was dissolved in 2 mL of toluene, and 130 mg of 3-thiophene carboxyaldehyde and then a catalytic amount of pyridinium p-toluene sulfonate were added and reacted at about 100C overnight, and then the reaction solution was left to cool. To the reaction solution, 50 mg of sodium borohydride and 2 mL of ethanol were added and reacted at room temperature for about two hours. Then, water and ammonium chloride were added in proper amounts, followed by stirring. A crude solution obtained by extraction with ethyl acetate was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to obtain 340 mg of N-(4-bromo-3,5-bis(trifluoromethyl)phenyl)-3-thiophene methanamine (melting point: 78-79C).

The synthetic route of 268733-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP2172456; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 268733-18-2,Some common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, molecular formula is C8H4BrF6N, 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.

synthesis of ethyl 5 -(4-amino-2, 6-bis(trifluoromethyl)phenyl)furan-2-carboxylate (143): 4-Bromo-3,5-bis(trifluoromethyl)aniline (142; 8 g, 26 mmol), 5- (ethoxycarbonyl)furan-2-ylboronic acid (7.2 g, 39 mmol), catalyst (2.1 g, 2.6 mmol) and K3P04 (16.5 g, 78 mmol) were added to a mixture of H20 (156 mL) and THF (300 mL). The mixture was degassed and stirred at room temperature for 2 h, extracted with EtOAc (300 mL X 2). The combined organic solvents were concentrated under reduced pressure and purified by silica gel chromatography (10-30% EtOAc/petroleum ether) to give 4.6 g of ethyl 5-(4- amino-2, 6-bi s(trifluoromethyl)phenyl)furan-2-carboxylate 143 as brown solid (48% yield). LCMS: m/z 368.0 [M+H], tR = 1.91 mm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3,5-bis(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (153 pag.)WO2017/31213; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary