Category: 175278-17-8

Adding a certain compound to certain chemical reactions, such as: 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 175278-17-8, Recommanded Product: 2-Bromo-4-(trifluoromethoxy)aniline

To a mixture of 2-bromo-4-(trifluoromethoxy)aniline (1.00 mmol), triethylamine (1.5 mmol) and P(o-tol)3 (0.40 mmol) in DMF (0.5 M) in a glass pressure tube under nitrogen gas were added ethyl acrylate (1.0 mmol) and palladium acetate (0.20 mmol). The tube was sealed and heated to 120 0C for 18 h. The resulting solution was concentrated under vacuum and purified by column chromatography. Retention time (min) = 2.467, method [1], MS(ESI) 276.1 (M+H).

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, 2-Bromo-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route 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.

Example 169 4- [3- (2-Bromo-4-trifluoromethoxy-phenyl)-ureido]-2-methoxy-benzoic acid methyl ester To a cooled (0C) solution of phosgene (20% solution in toluene, 2.76 ml, 5.52 mmol) in dry dichloromethane (75 ml) was added, under an argon atmosphere, methyl 4-amino-2- methoxybenzoate (1g, 5.52 mmol) in one portion, followed by a dropwise addition of diisopropylethylamine (1.92 ml, 11.04 mmol). The mixture was stirred for 15 minutes at 0C prior to the addition of 2-bromo-4 (trifluoromethoxy) aniline (0. 83 ml, 5.52 mmol). The reaction mixture was stirred at 0C for a further 2 hours and then was allowed to stir at room temperature overnight. The organic phase was washed with 1 N aq. HCI (2x), sat. aq. NaHCO3, dried over MgS04 and concentrated in vacuo to give a solid residue which was recrystallized in hot acetonitrile. The fine crystalline solid was filtered off, washed with cold acetonitrile and dried in vacuo to give the title compound Ex 169 as a pale-orange solid (1.64g, 3.54 mmol, 64%). ‘H-NMR (DMSO-d6) : J 3.74 (s, 3H), 3.80 (s, 3H), 7.02 (d, 1H), 7.38 (s, 1H), 7.42 (d, 1H), 7.69 (d, 1H), 7.74 (s, 1H), 8.17 (d, 1H), 8. 36 (s, 1H), 9.85 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-(trifluoromethoxy)aniline, its application will become more common.

Reference:
Patent; 7TM PHARMA A/S; WO2003/87045; (2003); 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. Computed Properties of C7H5BrF3NO

To a cooled (0C) solution of phosgene (20% solution in toluene, 2.76 ml, 5.52 MMOL) in dry DICHLOROMETHANE (75 ml) was added, under an argon atmosphere, methyl 4-amino-2- methoxybenzoate (1 G, 5.52 MMOL) in one portion, followed by a dropwise addition of diisopropylethylamine (1.92 ML, 11.04 MMOL). The mixture was stirred for 15 minutes at 0C prior to the addition of 2-bromo-4 (trifluoromethoxy) aniline (0.83 ML, 5.52 MMOL). The reaction mixture was stirred at 0C for a further 2 hours and then was allowed to stir at room temperature overnight. The organic phase was washed with 1 N aq. HCI (2x), sat. aq. NAHCO3, dried over MGS04 and concentrated in vacuo to give a solid residue which was recrystallized in hot acetonitrile. The fine crystalline solid was filtered off, washed with cold acetonitrile and dried in vacuo to give the title compound Ex 106 as a pale-orange solid (1. 64G, 3.54 mmol, 64%). ‘H-NMR (DMSO-d6) : 6 3.74 (s, 3H), 3.80 (s, 3H), 7.02 (d, 1H), 7.38 (s, 1H), 7.42 (d, 1H), 7.69 (d, 1H), 7.74 (s, 1H), 8.17 (d, 1H), 8.36 (s, 1H), 9.85 (s, 1H)

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; 7TM PHARMA A/S; LITTLE, Paul Brian; WO2004/48319; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 175278-17-8, These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)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: Triphosgene (0.09 g, 0.3 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 (0.16 g, 0.7 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.12 mL, 0.89 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.12 mL, 0.89 mmol), compound (9) (0.2 g, 0.74 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 = 3:1) yielding (W1).

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

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
Ether – Wikipedia,
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Electric Literature 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 mixture of 2-bromo-4-(trifluoromethoxy)aniline 17 (Maybridge, 2.048 g, 8.00 mmol), methyl acrylate (1.80 mL, 20.0 mmol), Pd(OAc)2 (215.5 mg, 0.960 mmol), tri-o-tolylphosphine (1.169 g, 3.84 mmol), and dry Et3N (4.30 mL, 30.9 mmol) in dry CH3CN (16.0 mL) was stirred under reflux conditions under N2 for 4 h, then concentrated in vacuo. The residue was partitioned between H2O (30 mL) and AcOEt (30 mL). The organic layer was separated and the aqueous layer was extracted with AcOEt (30 mL × 2). The organic layers were combined, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to afford 3.630 g of the title product 21 (crude). This compound was used for the next step without further purification. 1H NMR (270 MHz, CDCl3) delta 7.74 (1H, d, J = 15.8 Hz), 7.23-7.02 (2H, m), 6.68 (1H, d, J = 8.72 Hz), 6.36 (1H, d, J = 15.8 Hz), 4.00 (2H, br s), 3.81 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-(trifluoromethoxy)aniline, its application will become more common.

Reference:
Article; Hayashi, Shigeo; Ueno, Naomi; Murase, Akio; Nakagawa, Yoko; Takada, Junji; European Journal of Medicinal Chemistry; vol. 50; (2012); p. 179 – 195;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 175278-17-8, These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)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.

EXAMPLE 94 2-[(phenylsulfonyl)amino]-4-(trifluoromethoxy)benzoic acid The desired product was prepared by substituting 2-bromo-4-(trifluoromethoxy)aniline for 2-bromo-4-isopropylaniline in Examples 2A-D. MS (ESI(+)) m/e 362 (M+H)+, 379 (M+NH4)+, 384 (M+Na)+; (ESI(-)) m/e 360 (M-H)-; 1H NMR (300 MHz, DMSO-d6) delta 7.76 (m, 1H), 7.73 (m, 1H), 7.68 (m, 1H), 7.51 (m, 3H), 7.39 (d, 1H), 7.20 (m, 1H).

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

Reference:
Patent; Comess, Kenneth M.; Erickson, Scott A.; Henkin, Jack; Kalvin, Douglas M.; Kawai, Megumi; Kim, Ki H.; BaMaung, Nwe Y.; Park, Chang Hoon; Sheppard, George S.; Vasudevan, Anil; Wang, Jieyi; Barnes, David M.; Fidanze, Steve D.; Kolaczkowski, Lawrence; Mantei, Robert A.; Park, David C.; Sanders, William J.; Tedrow, Jason S.; Wang, Gary T.; US2004/157836; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)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. category: ethers-buliding-blocks

Intermediate 1: 2-propyl-4-(trifluoromethoxy)aniline A solution of 2-bromo-4-(trifluoromethoxy)aniline (256 mg, 1.00 mmol), [(E)-prop-1-enyl]boronic acid (172 mg, 2.00 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (29.0 mg, 0.0400 mmol), and K2CO3(aq) (1 M, 2 equiv) in MeOH (0.5 mL)/toluene (0.5 mL) was stirred at 125 C. for 4 h. The organic layer was separated, concentrated to dryness, and purified by FCC (SiO2) to give (E)-2-(prop-1-en-1-yl)-4-(trifluoromethoxy)aniline. (E)-2-(Prop-1-en-1-yl)-4-(trifluoromethoxy)aniline and Pd/C (10% on carbon, 30 mg) in MeOH (10 mL) was stirred under H2 (1 atm) for 3 h. After filtration on diatomaceous earth such as Celite, the filtrate was collected and concentrated to dryness to give 2-propyl-4-(trifluoromethoxy)aniline. MS (ESI): mass calcd. for C10H12F3NO, 219.1; m/z found, 220.1 [M+H]+.

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

Reference:
Patent; Janssen Pharmaceutica NV; Bacani, Genesis M.; Chai, Wenying; Edwards, James P.; Smith, Russell C.; Tichenor, Mark S.; Venable, Jennifer D.; Wei, Jianmei; (64 pag.)US2018/289706; (2018); 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.

A solution of commercially available 2-bromo-4-(trifluoromethoxy)aniline (theproduct of step 1, Example 55, 4.00 g, 15.63 mmol) in DMF (1 0 mL) was addedslowly to a suspension of NaH (60% in mineral oil, 1.13 g, 46.88 mmol) in DMF(20 mL) at 0C. After warming to room temperature the reaction mixture wasstirred for 30 minutes. Commercially available tert-butyl 4-(chloromethyl)-5,6-dihydropyridine-1 (2H)-carboxylate (3.62 g, 15.63 mmol) in DMF (1 0 mL) was added and the mixture stirred at room temperature for 1 hour. Cold water (100 mL) was added and the mixture extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with cold water (2 x 50 mL) and brine(5OmL), dried over anhydrous sodium sulphate and concentrated. The crudematerial was purified by flash chromatography eluting with 20% ethylacetate/hexane to afford the title compound as grey solid (2.5 g, 36%): 1 H NMR(400 MHz, DMSO-d6) oe: 1 .38 (5, 9 H), 1 .99 (bs, 2 H), 3.39 (t, 2 H), 3.75 (bs, 4 H),5.50 (5, 1 H), 5.79 (t, 1 H), 6.60 (d, 1 H), 7.17 (d, 1 H), 7.47 (d, 1 H). LC-Ms(m/z): [M-H] = 448.8.

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; ZOETIS SERVICES LLC; WENDT, John; COX, Mark; SHEEHAN, Susan, M.k.; CURTIS, Michael, P.; RESPONDEK, Tomasz; EWIN, Richard, Andrew; KYNE, Graham, M.; JOHNSON, Paul, D.; WO2015/100232; (2015); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 175278-17-8, name is 2-Bromo-4-(trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 175278-17-8, Formula: C7H5BrF3NO

General procedure: 1,1-Cyclopropanedicarboxylic acid (5) (12.0 g, 15.4 mmol) was dissolved in anhydrous THF (50 mL). Then triethanolamine (2.0 mL,13.9 mmol) was added to the mixture and the mixture was stirred on the ice-bath for 30 min. SOCl2 (1.2 mL, 16.66 mmol) was then added. Stirring was continued for 2h, a solution of 3,5-dimethylaniline 6 (3.6 g, 15.4 mmol) in anhydrous THF (10 mL) was added and continued stirring for 2h, after that, the ice bath was removed, and the mixture was stirred at room temperature overnight. After the completion of the reaction, the mixture was filtered and concentrated in vacuo. The residues was purified by silica gel flash chromatography (PE/AcOEt = 5:1) to yield 7 as white solid (0.8 g, 30.7%).

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, 2-Bromo-4-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Chuansheng; Shan, Yuanyuan; Sun, Ying; Si, Ru; Liang, Liyuan; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 506 – 518;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference 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: Tert-butyl (R)-(5-(trimethylsilyl)pent-4-yn-2-yl)carbamate (160 mg, 0.63 mmol) was added in DMF (2.5 mL) to a sealed vial containing amino-halide (0.5 mmol), sodium carbonate (106 mg, 1.00 mmol), lithium chloride (21.00 mg, 0.50 mmol) and Pd(dppf)Cl2.CH2Cl2 (14.62 mg, 0.02 mmol). The reaction was degassed for 10 min, then heated to 100 C for 4 hours. After cooling, the reaction was diluted with EtOAc and washed with water and brine. The organic was dried over Na2SO4 and evaporated, then the crude product was purified by flash silica chromatography (EtOAc / heptane). Pure fractions were evaporated to dryness to afford the indole.

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

Reference:
Article; Moss, Thomas A.; Lister, Andrew S.; Wang, Jimmy; Tetrahedron Letters; vol. 58; 32; (2017); p. 3136 – 3138;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem