Category: 175278-17-8

Application of 175278-17-8, A common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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: Triphosgene (0.14 g, 0.48 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.3 g, 1.2 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.2 mL, 1.44 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.2 mL, 1.44 mmol), 4-pyridin-3-ylaniline (5) (0.2 g, 1.2 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 6:1) yielding (L1). yield 73%

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference of 175278-17-8,Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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.

A solution of 2-bromo-4-(trifluoromethyloxy)aniline (5.1 g), in 1 ,4-dioxane (30 ml.) was treated with bis(trichloromethyl) carbonate (2.2g). The mixture was heated to 1000C to give a clear solution then allowed to cool to ambient temperature. The solvent was evaporated and the residue was dissolved in dichloromethane (70ml) and 1 ,1- dimethylethyl 4-amino-1 -piperidinecarboxylate (4.0 g) was added. The mixture was stirred overnight at room temperature. Silica gel was added and the solvent was evaporated. The residue was loaded onto a silica gel chromatography column which was eluted with hexane/ethyl acetate 0-100% followed by chromatography on silica gel eluted with dichloromethane/methanol 0-10% to give the title compound as a white solid from diethyl ether (4.3 g).1HNMR delta (DMSO, 400 MHz): 1.25 (2H, m), 1.40 (9H, s), 1.79 (2H, m), 2.93 (2H, broad), 3.64 (1 H, m), 3.80 (2H, m), 7.21 (1 H, d), 7.35 (1 H, d), 7.66 (1 H, s), 7.91 (1 H, s), 8.19 (1 H, d).

The synthetic route of 175278-17-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2007/107565; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 175278-17-8, 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. 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 2-bromo-4-trifluoromethoxyaniline (0.500 g), cupper iodide (I) (18.6 mg), bis(triphenylphosphine)palladium (II) dichloride (68.5 mg), triethylamine (0.817 mL) and tetrahydrofuran (7.8 mL) was added phenylacetylene (0.279 mL) at room temperature under stirring, and the mixture was stirred at 80 C. for 16 hours. The reaction mixture was cooled to room temperature, diluted with diethyl ether (30 mL) and then filtered through celite (registered trademark). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (206 mg).1H-NMR (CDCl3) delta ppm:4.32 (2H, br s), 6.70 (1H, d, J=8.8 Hz), 6.95-7.10 (1H, m), 7.20-7.30 (1H, m), 7.30-7.45 (3H, m), 7.45-7.60 (2H, m).

The synthetic route of 2-Bromo-4-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KISSEI PHARMACEUTICAL CO., LTD.; US2012/129890; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 175278-17-8, 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. 175278-17-8 name is 2-Bromo-4-(trifluoromethoxy)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 anhydrous copper [(II)] chloride (6.3g, 47mmol) in acetonitrile (lOOmL) was added tert-butyl nitrite (6.85mL, [58MMOL),] followed dropwise by a solution of [2-BROMO-4- (TRIFLUOROMETHOXY)] aniline (lOg, 39mmol) in acetonitrile [(15ML).] The solution was stirred at ambient temperature for 1 hour then poured into hydrochloric acid (250mL, 2M). The suspension formed was extracted with diethyl ether [(2X250ML)] and the extracts were dried [(MGS04).] Concentration yielded the title compound as an oil (7.82g, [28MMOL).] [ON] (360 MHz, [CDCL3)] : 7.51 [(1H,] d, J 3.2Hz), 7.48 [(1H,] d, J 8.8Hz), 7.15 [(1H,] dd, J 3.2 and 8.8Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/31190; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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. category: ethers-buliding-blocks

According to route (C), 2-bromo-4-trifluoromethoxyaniline (2.3 mL, 15 mmoles, 1 eq.) was placed in l,4-dioxane (55 mL) with Pd(dppf)Cl2.CH2Cl2 (1.2 g, 1.5 mmole, 0.1 eq.). Upon addition of CS2CO3 (19.6 g, 60 mmoles, 4 eq.) and ethylboronic acid (3.3 g, 45 mmoles, 3 eq.), the reaction mixture was heated at l00C and stirred for 14 hours under an inert atmosphere of argon. The reaction mixture was then concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to afford 2-ethyl-4-(trifluoromethoxy)aniline (1.3 g, 42%). (0391) 6.93 (s, 1H), 6.90 (d, J = 8.5 Hz, 1H), 6.63 (d, J = 8.5 Hz, 1H), 3.64 (s, 2H), 2.49 (q, 7 = 7.5 Hz, 2H), 1.25 (t , J= 7.5 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 175278-17-8, its application will become more common.

Reference:
Patent; ABIVAX; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE MONTPELLIER; INSTITUT CURIE; SCHERRER, Didier; TAZI, Jamal; MAHUTEAU-BETZER, Florence; NAJMAN, Romain; SANTO, Julien; APOLIT, Cecile; (0 pag.)WO2020/11810; (2020); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem