Author: Jessica.F

Application of 578-57-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 578-57-4, name is 1-Bromo-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

n-BuLi (3.5 ml of a 1.6 M solution in hexane) was added with stirring at 0 C to a solution of 2-bromoanisole (1.0 g, 5.34 mmol) in dry hexane (10 ml) and the mixture was allowed to stir at room temperature. After 2 h stirring the n-butyl bromide formed in the reaction mixture was evaporated under reduced pressure without introduction of air. Dry THF (10 ml) was added followed by the addition of the finely ground selenium powder (0.42 g, 5.34 mmol) at 0 C. It was stirred for 4 h. It was poured to the ice-cooled saturated NaHCO3 solution and O2 gas was passed to the mixture in a moderate rate for 15 min. The compound was extracted with diethyl ether and dried with anhydrous Na2SO4. The solvent was evaporated to obtain yellow-colored solid. The compound was purified in flash chromatography using petroleum ether and ethyl acetate as solvent. It was characterized by NMR spectroscopy. Yield: 0.58 g (31%), 1H NMR (CDCl3), delta (ppm): 3.91 (s, 6H, OCH3), 6.80-6.83 (d, 2H, ArH), 6.85-6.89 (m, 2H, ArH), 7.19-7.23 (m, 2H, ArH), 7.53-7.55 (d, 2H, ArH); 13C NMR (CDCl3), delta (ppm): 56.4, 110.6, 119.1, 122.4, 128.6, 131.0, 157.3; 77Se NMR (CDCl3), delta (ppm): 328. ESI-MS: m/z: calcd for C14H13O2Se2 [M+Na]+: 396.9222; found: 397.0495.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bhowmick, Debasish; Mugesh, Govindasamy; Tetrahedron; vol. 68; 51; (2012); p. 10550 – 10560,11;,
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Related Products of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: To asolution of hydrazide (0.73 mmol) in 10 mL of anhydrous ethanol, added triethyl orthoester (0.81 mmol) and ammonium chloride (0.219 mmol). The solution was stirred and heated to reflux until it complete (0.5-18 h). The reaction mass was cooled to room temperature and concentrated under vacuum. The crude product was made into slurry in a mixture of hexanes and ether (3:1), filtered,washed with deionized water or purified by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Triethoxymethyl)benzene, its application will become more common.

Reference:
Article; Gnanasekaran, Krishna Kumar; Nammalwar, Baskar; Murie, Maeghan; Bunce, Richard A.; Tetrahedron Letters; vol. 55; 50; (2014); p. 6776 – 6778;,
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Adding a certain compound to certain chemical reactions, such as: 2752-17-2, name is 2,2′-Oxydiethanamine, 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 2752-17-2, COA of Formula: C4H12N2O

Mixed nanosized TiO2-SiO2 oxide (0.27 g, 1.9 mmol) was added to a solution of acetoacetic ester (2) (3.75 g,28.8 mmol), 1,5-diamino-3-oxapentane (1a) (1.00 g, 9.6 mmol), and toluene (6 ml). The reaction mixture was stirred for 20 h at 90C. After the reaction was complete (TLC control, eluent 5:4:1 EtOAc-hexane-CHCl3), the nanosized oxide was separated by centrifugation, and toluene was removed by distillation. The obtained oil was purified by silica gel column chromatography, using CHCl3 as eluent, and dried under ambient conditions. Yield 2.33 g (74%), yellow oil. IR spectrum, nu, cm-1: 1141 (nuas, –Alk); 3291 (N-H); 1652,1505 (-O-N); 2930, 2978 (Alk-). 1H NMR spectrum,delta, ppm: 1.12-1.14 (6H, m, 2CH3); 1.90 (6H, s, 2CH3); 3.35-3.39 (4H, m, 2NCH2CH2); 3.51-3.55 (4H, m, 2NCH2CH2); 3.92-3.97 (4H, m, 232); 4.34-4.35 (2, m, 2); 8.59 (2H, s, 2NH). Found, %: 58.46; 8.43; N 8.69.16H28N2O5. Calculated, %: 58.51; 8.59; N 8.53.

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; Radionova, Elena S.; Fedorova, Olga V.; Titova, Yulia A.; Rusinov, Gennady L.; Charushin, Valery N.; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 478 – 482; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 478 – 482,5;,
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Application of 645-36-3,Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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 1,4-dimethyl-3-formylcarbazole (500 mg, 2.2 mmol) in benzene (15 mL) and 2,2-diethoxyethylamine (330 mg, 2.5mmol) was placed in a flask. The mixture was refluxed for 2 h. After the reaction, the solvent was evaporated under the reduced pressure. MeOH (15 mL) was added to the residue. NaBH4 (800 mg, 22mmol) was then added slowly, and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated under the reduced pressure. The residue was extracted with CHCl3 and dried over Na2SO4, andconcentrated under reduced pressure. A solution of the residue in a mixture of MeCN (10 mL) andpyridine (1 mL) was placed in a flask. After the solution was stirred at rt for 0.5 h, 2-nitrobenzenesulfonylchloride (1.0 g, 4.5 mmol) was added, and the reaction mixture was stirred at rt for 24 h. After thereaction, the solvent was evaporated under reduced pressure. The crude product was recrystallized from MeOH, affording N-(2,2-diethoxyethyl)-N-((1,4-dimethyl-9H-carbazol-3-yl)methyl)-2-nitrobenzenesulfonamide (85%, 1.0 g); yellow solid; mp 175.0-176.0 C; 1H NMR (500 MHz, CDCl3) delta 1.46 (6H, t, J= 7 Hz), 2.41 (3H, s), 2.73 (3H, s), 3.41-3.46 (4H, m), 3.61-3.64 (2H, m), 4.56 (1H, t, J = 5.5 Hz), 4.88(2H, s), 7.07 (1H, s), 7.21-7.26 (1H, m), 7.36-7.42 (2H, m), 7.47 (1H, d, J = 8 Hz), 7.52 (1H, d, J = 8 Hz),7.60 (1H, d, J = 8 Hz), 7.77 (1H, d, J = 8 Hz), 8.03 (1H, brs), 8.15 (1H, d, J = 8 Hz); 13C NMR (CDCl3,125 MHz) delta 15.3, 15.9, 16.5, 49.6, 50.6, 63.4, 102.2, 110.6, 116.8, 119.5, 121.9, 122.8, 123.7, 123.8,124.3, 125.1, 128.7, 130.4, 130.8, 131.1, 132.8, 134.4, 138.4, 139.6, 147.8; MS (FAB+) m/z 525 [M+];HRMS (FAB+): calcd for C27H31N3O6S (M+) 525.1933, found 525.1921.

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

Reference:
Article; Sato, Naoya; Kawai, Yu; Akaba, Yosuke; Honma, Shoji; Sakai, Norio; Konakahara, Takeo; Heterocycles; vol. 92; 4; (2016); p. 664 – 679;,
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Related Products of 150-78-7, These common heterocyclic compound, 150-78-7, name is 1,4-Dimethoxybenzene, 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: To a stirred solution of starting compound (0.5-1.2 mmol) in DMF-H2O (95:5, v/v, 8-12 mL) mixture was added NBS (4.0-4.2 mmol) at room temperature. The contents were stirred at room temperature about 10 min and then heated for appropriate duration mentioned in Table 2. Progress of the reaction in every case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and quenched with aqueous NaHCO3 (20%, 20-30 mL) solution. The insoluble precipitate was isolated by filtration and dried in vacuo. It was further purified by either recrystallization with ethyl acetate/n-hexane mixture or short pad silica gel column chromatography led to pure product.

The synthetic route of 150-78-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Natarajan, Palani; Vagicherla, Vinuta Devi; Vijayan, Muthana Thevar; Tetrahedron Letters; vol. 55; 24; (2014); p. 3511 – 3515;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 171290-52-1

Cul (0.053g, 0.2mmol) was added to the degassed solution of 5-Iodo-N-(2-methyl-6- nitrophenyl)pyrimidin-2-amine (lg, 2.8mmol) and l-ethynyl-3,5-dimethoxybenzene (0.5g, 3.0mmol) in DMF (5mL) followed by the addition of tetrakis (0.32g, 0.2mmol) in a sealed tube. Stirred the reaction mass for 10 min and added DIPEA (0.75mL, 4.2mmol) and heated the resultant reaction mass to 80 C for 2h. Reaction mass was filtered through celite and washed the celite bed with ethyl acetate. The organic layer washed with water followed by brine, dried over Na2S04, filtered and concentrated. The residue was purified by 60-120 silica gel column chromatography to afford desired title compound (0.7g, 66%). LCMS: m/z = 391.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 171290-52-1.

Reference:
Patent; EISAI R & D MANAGEMENT CO., LTD.; REYNOLDS, Dominic; HAO, Ming-Hong; WANG, John; PRAJAPATI, Sundeep; SATOH, Takashi; SELVARAJ, Anand; (128 pag.)WO2016/164703; (2016); A1;,
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Application of 168268-00-6,Some common heterocyclic compound, 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, molecular formula is C13H12FNO, 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 4-benzyloxy-3-fluoroaniline (6.06 g, 27.9 mmol) (U.S. Pat. No. 5,622,967) and ethyl (ethoxymethylene)cyanoacetate (5.08 g, 30.0 mmol) is heated at 120 C. for 45 minutes then cooled to room temperature. This solid is added in portions to a 3:1 mixture of diphenyl ether:biphenyl at 245 C. This mixture is heated at 245 C. for 3 hours then cooled and the solids are collected by filtration, washing with hexane and diethyl ether to provides 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4-dihydro-3-quinolinecarbonitrile, mp>250 C. [0198] MS 293.1 (M-H)-

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

Reference:
Patent; Wyeth Holdings Corporation; US2003/212276; (2003); A1;,
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Application of 22236-10-8,Some common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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-[(fert-butyldimethylsilyloxy)methyl]-3-(4,6-dichloro-5- fluoropyrimidin-2-yl)-5-fluoropyrazolo[l,5-a]pyridine (102.0 mg, 0.23 mmol), 4- difluoromethoxy aniline (145.0 mg, 0.92 mmol) and ethanol (1 mL) was heated at 90C overnight. After cooling, the mixture was poured into ice- water to afford a solid. The solid was collected by filtration, followed by washing with water and hexane. The solid was dried under the vacuum to provide 2-[2-[(teri-butyldimethylsilyloxy)methyl]-5-fluoropyrazolo[l,5- a]pyridin-3-yl]-6-chloro-N-(4-difluoromethoxy)phenyl]-J-fluoropyrimidin-4-amine (a mixture of TBS protected and unprotected product).

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; LEE, Chang-Sun; BAIAZITOV, Ramil; CAO, Liangxian; DAVIS, Thomas, W.; DU, Wu; LIU, Ronggang; MOON, Young-choon; PAGET, Steven, D.; REN, Hongyu; SYDORENKO, Nadiya; WILDE, Richard, Gerald; WO2014/81906; (2014); A2;,
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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. 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Formula: C8H9FO2

To a solution of 1-fluoro-3,5-dimethoxybenzene (12.5 g, 80.0 mmol) in dichloromethane (80 ml), cooled to 0 C, was added a 1.0 M solution of BBr3 in dichloromethane (200 ml, 200 mmol), dropwise over a 30 minutes period. The reaction was stirred for 1 hour at 0 C and then slowly warmed to room temperature and stirred for 18 hours. The reaction was cooled to 0 C and quenched by slow addition of MeOH and water. After stirring at room temperature for 1 hour the mixture was filtered and volatiles were removed in vacuo. The solid was washed twice with ethyl acetate; the filtrate was concentrated in vacuo to provide intermediate 8-b as an orange solid.

The synthetic route of 52189-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMASCIENCE INC.; LAURENT, Alain; ROSE, Yannick; WO2014/5217; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 888327-32-0, name is 4-Bromo-1-(difluoromethoxy)-2-methylbenzene, 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 888327-32-0, COA of Formula: C8H7BrF2O

EXAMPLE 71 Preparation of 2-Amino-5,5-bis-[4-(difluoromethoxy)-3-methylphenyl]-3-methyl-3,5-dihydro-4H- imidazol-4-one; Step 1 : bis(4-difluoromethoxy-3-methyl-phenyl)acetyleneIn a CEM snap top microwave vial were combined trimethylsilylacetylene (0.207 g, 2.11 mmol), 4-Bromo-1-difluoromethoxy-2-methyl-benzene (1.00 g, 4.22 mmol), tetrakis(triphenylphosphine)palladium (56 mg, 0.0485 mmol) and pyrrolidine (1 ml_, 12 mmol).The reaction vial was placed in a CEM Explorer microwave and irradiated for 30 minutes at 8O0C. The crude reaction mixture was poured directly onto silica gel and purified by column chromatography (hexanes) to yield 0.519 g of 1 ,1′-(1.2-ethynediyl)bis[4-difluoromethoxy-3- methylbenzene] as a clear oil (73%). 1H NMR (400 MHz, DMSO-cfe) delta ppm 2.24 (s, 6 H) 7.19 (d, 2 H) 7.26 (t, J=73.7 Hz, 2H) 7.44 (q,J=8.6, 2.1 Hz, 2 H) 7.51 (d, J=1.4 Hz, 2 H); MS (El) m/z 338 [M+.]

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-1-(difluoromethoxy)-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2008/115552; (2008); A1;,
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