Category: 402-07-3

Adding a certain compound to certain chemical reactions, such as: 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, 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 402-07-3, Recommanded Product: 402-07-3

General procedure: A microwave vial was charged with N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (28) (0.100 g, 0.24 mmol), xantphos (0.028 g, 0.048 mmol), 4-bromo-3-methoxybenzonitrile (0.051 g, 0.24 mmol), Pd2(dba)3 (0.022 g, 0.024 mmol) and sodium tert-butoxide (0.046 g, 0.48 mmol). The mixture was diluted with toluene (2.5 mL), purged with nitrogen, and heated at 130 C in the microwave for 30 min. After completion, the mixture was cooled to room temperature and trifluoroacetic acid (1.0 mL) was added. After stirring for 45 min at room temperature, the reaction was filtered through a plug of Celite, washing with DCM 10 mL). The filtrate was concentrated and purified by reverse-phase preparative HPLC using 0.1% TFA in CH3CN/H2O, gradient 25% to 90% over 15 min to provide 4-(4-cyano-2-methoxyphenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide 10 as a salt with trifluoroacetate (0.073 g, 0.14 mmol, 56 % yield) as an orange solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; La, Daniel S.; Peterson, Emily A.; Bode, Christiane; Boezio, Alessandro A.; Bregman, Howard; Chu-Moyer, Margaret Y.; Coats, James; DiMauro, Erin F.; Dineen, Thomas A.; Du, Bingfan; Gao, Hua; Graceffa, Russell; Gunaydin, Hakan; Guzman-Perez, Angel; Fremeau, Robert; Huang, Xin; Ilch, Christopher; Kornecook, Thomas J.; Kreiman, Charles; Ligutti, Joseph; Jasmine Lin, Min-Hwa; McDermott, Jeff S.; Marx, Isaac; Matson, David J.; McDonough, Stefan I.; Moyer, Bryan D.; Nho Nguyen, Hanh; Taborn, Kristin; Yu, Violeta; Weiss, Matthew M.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3477 – 3485;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

402-07-3, 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 402-07-3 as follows.

To a solution of 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (69.0 mg, 0.27 mmol) in dry THF (4 mL) at -78 C under N2 was slowly added N-BuLi (0.11 mL, 2.5 M in N-pentane, 0.27 mmol). After being stirred for 30 min, a solution of 8 (50 mg, 0.11 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4Cl (15 mL) solution, and extracted with EtOAc (10 mL ¡Á 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtOAc/petroleum ether, Rf = 0.2) to give 25 (56 mg, 81%) as a pale brown solid. mp 34.7-36.7 C; 1H NMR (400 MHz, CDCl3) delta 0.001 (s, 3H), 0.07 (s, 3H), 0.83 (s, 9H), 2.41 (s, 3H), 2.94 (d, J = 4.0 Hz, 1H), 3.73 (s, 3H), 4.43 (d, J = 12.0 Hz, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.81-5.84 (m, 2H), 6.10 (t, J = 3.2 Hz, 1H), 6.34 (d, J = 3.6 Hz, 1H), 6.66 (dd, J = 3.6, 2.0 Hz, 1H), 6.99 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 3.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H) ppm; 13C NMR (CDCl3, 100 MHz) delta -5.71, -5.67, 18.53, 21.56, 25.92, 25.92, 25.92, 53.27, 55.53, 62.79, 106.87, 106.91, 108.05, 108.43, 111.37, 117.21, 117.25, 121.56, 123.91, 126.96, 127.01, 127.35, 128.40, 129.44, 129.87, 134.75, 134.76, 135.81, 136.29, 145.17, 156.02 ppm; HRMS (M + Na+) calcd. for C31H37F3N2NaO5SSi 657.2042, found 657.2040; IR (KBr) 3383, 3146, 2956, 2929, 2857, 1734, 1594, 1465, 1415, 1377, 1329, 1241, 1175, 1123, 1032, 841, 778, 670 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 402-07-3, and friends who are interested can also refer to it.

Reference:
Article; Cheng, Chunwei; Liu, Yan; Song, Hao; Pan, Lili; Li, Jerry; Qin, Yong; Li, Rongshi; Marine Drugs; vol. 11; 8; (2013); p. 2927 – 2948;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

402-07-3, The chemical industry reduces the impact on the environment during synthesis 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, I believe this compound will play a more active role in future production and life.

A vial was charged with 6-bromo-N-(4-methoxybenzyl)-N-(thiazol-2-yl)- 3,4-dihydro-2H-benzo[b][l,4]oxazine-7-sulfonamide (107.43 mg, 0.216 mmol), l-bromo-2-methoxy-4-(trifluoromethyl)benzene (Sigma-Aldrich, St. Loius, MO, 193 mg, 0.757 mmol), Xantphos (25.04 mg, 0.043 mmol), Pd2(dba)3 (19.82 mg, 0.022 mmol), and cesium carbonate (212 mg, 0.649 mmol). The vessel was flushed with Ar (g), then 1,4-dioxane (2164 mu) was added. The vessel was sealed and placed in a 100 C heating bath for 20 h. The mixture was cooled to room temperature, diluted with EtOAc, and filtered through celite. The filtrate was concentrated, and the residue was purified by chromatgraphy on silica gel (12-g Redi-Sep Gold column, 0-50% EtO Ac/Heptane) to give 6-bromo-4-(2-methoxy-4- (trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H- benzo[b][l,4]oxazine-7-sulfonamide (67 mg, 0.100 mmol, 46.2 % yield) as a yellow foam: m/z (ESI) 670.2 (M+H)+

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methoxybenzotrifluoride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; BOEZIO, Christiane; BOEZIO, Alessandro; BREGMAN, Howard; CHAKKA, Nagasree; COATS, James R.; COPELAND, Katrina W.; DIMAURO, Erin F.; DINEEN, Thomas; GAO, Hua; LA, Daniel; MARX, Isaac E.; NGUYEN, Hanh Nho; PETERSON, Emily Anne; WEISS, Matthew; WO2013/122897; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

402-07-3,Some common heterocyclic compound, 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, molecular formula is C8H6BrF3O, 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 (2-(Hydroxy(2-methoxy-4-(trifluoromethyl)phenyl)methyl)- 1 ‘-tosyl-l – 1 ,3 ‘- bipyrrol-2’-yl)(2-methoxy-4-(trifluoromethyl)phenyl)methanone (37). To a solution of l-bromo-2-methoxy-4-(trifiuoromethyl)benzene (720 mg, 2.88 mmol) in dry THF (5 mL) at -78 C under N2 was slowly added n-BuLi (1.15 mL, 2.5 M in n-pentane, 2.88 mmol). After being stirred for 30 min, a solution of 36 (550 mg, 1.06 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4C1 (15 mL) solution and extracted with EtO Ac (10 mL x 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtO Ac/petroleum) to give 37 (400 mg, 54% yield) as a light yellow solid. 1H NMR (400 MHz, CDCI3) delta 2.44 (s, 3H), 3.59 (br s, 3H), 3.84 (s, 3H), 5.77 (br s, 1H), 6.17-6.32 (m, 3H), 6.49 (br s, 1H), 6.70 (br s, 1H), 6.83 (d, J= 7.6 Hz, 1H), 7.13 (br s, 1H), 7.21 (br s, 1H), 7.35-7.37 (m, 4H), 7.42 (d, J= 2.8 Hz, 1H), 7.92 (d, J= 8.0 Hz, 2H) ppm; 13C NMR (CDC13, 100 MHz) delta 21.67, 55.75, 55.88, 67.96, 105.60, 105.64, 108.13, 108.03, 111.28, 116.78, 116.78, 116.78, 120.85, 120.85, 124.97, 126.20, 127.10, 127.30, 127.63, 127.63, 129.14, 129.14, 129.98, 129.98, 132.50, 132.56, 133.21, 133.45, 135.92, 145.38, 155.48, 157.01, 180.50 ppm; IR (KBr) 3444, 3137, 2923, 1668, 1562, 1447, 1361, 1180, 1014, 752, 668 cm”1.

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-methoxybenzotrifluoride, its application will become more common.

Reference:
Patent; CHONGQING ZEIN PHARMACEUTICAL CO., LTD.; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; QIN, Yong; CHENG, Chunwei; SONG, Hao; LI, Rongshi; LIU, Yan; WO2014/116634; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem