Category: ethers-buliding-blocks

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. 589-10-6, name is (2-Bromoethoxy)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9BrO

To a stirred solution of (2-bromoethoxy)benzene (1 g, 5 mmol) in CH3CN (50 mL) wereadded methyl piperidine-4-carboxylate (0.715g, 5 mmol, 1 equiv) and sodium bicarbonate (1.26 g, 15 mmol, 3 equiv) at room temperature. The reaction mixture was heated atlOOand stirred for 16 h. After completion, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic extract was washed with brine, filtered and dried over sodium sulphate. The solvent was removed under reduced pressure. Purificationusing silica gel column chromatography (20% EtOAc Hexanes as eluent) afforded 1 gmethyl 1-(2-phenoxyethyl) piperidine-4-carboxylate (Yield = 76%). ESI+ MS: m/z: 264.1 ([M+Hj).

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:
Patent; THE BROAD INSTITUTE, INC.; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOLSON, Edward; WAGNER, Florence, Fevrier; WEIWER, Michel; SCOLNICK, Edward; PALMER, Michelle; LEWIS, Michael; PAN, Jennifer, Q.; ZHANG, Yan-Ling; XU, Qihong; (323 pag.)WO2016/100823; (2016); A1;,
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Related Products of 651734-54-2,Some common heterocyclic compound, 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline, molecular formula is C8H9F2NO2, 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. 4-Chloro-N-(2,6-difluoro-3,5-dimethoxyphenyl)thieno[3,2-d]pyrimidine-7-carboxamide 4-Chlorothieno[3,2-d]pyrimidine-7-carboxylic acid (23 mg, 0.10 mmol) prepared in step g of Example 107, 2,6-difluoro-3,5-dimethoxybenzene amine (19 mg, 0.10 mmol), and HOBT (N-hydroxybenzotriazole, 13.5 mg, 0.10 mmol) were dissolved in acetonitrile (2 mL), and EDCI (57 mg, 0.30 mmol) was added thereto at room temperature. After 15 hrs, water and ethyl acetate were added to the reaction mixture. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with a saline solution, dried over magnesium sulfate, and concentrated under a reduced pressure. The resulting concentrate was purified by silica gel chromatography (DCM:MeOH=20:1) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) delta 10.69 (s, 1H), 9.39 (s, 1H), 8.88 (s, 1H), 7.02 (s, 1H), 3.84 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluoro-3,5-dimethoxyaniline, its application will become more common.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; HANMI PHARM. CO. LTD.; US2012/302567; (2012); A1;,
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Synthetic Route of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

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, 5-Bromo-2-(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;,
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Reference of 54149-17-6,Some common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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.

To a solution of 2-hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde from EX-LB (0.10 g, 0.43 mmol) in N, N-DIMETHYLFORMAMIDE (3 mL) was added potassium carbonate (0.18 g, 1.3 mmol) and the resulting yellow slurry was heated to 80C. Once at 80 C, 1-BROMO-2-(2-METHOXYETHOXY) ethane (0.24 g, 1.3 mmol) was added dropwise in three equal portions with stirring at 1 h intervals. After the last addition, the reaction was stirred for an additional 1 h at 80 C and cooled to room temperature. The mixture was diluted with water (15 mL) and extracted with ethyl acetate (3 x 15 mL). The combined organic layers was sequentially washed with a saturated ammonium chloride solution (1 X 15 mL), water (1 X 15 mL), and brine (1 X 15 mL), dried over sodium sulfate, and concentrated to a brown oil. Silica gel chromatography (ethyl acetate/hexanes, 4: 1) afforded 0.13 g (87%) of 4-METHOXY-2- [2- (2- methoxyethoxy) ethoxy] -5-thiophen-2-yl-benzaldehyde as a pale yellow OIL.’H-NMR (300 MHz, CDC13) 8 10.38 (s, 1 H), 8.12 (s, 1 H), 7.44 (dd, 1 H), 7.30 (dd, 1 H), 7.07 (dd, 1 H), 6.57 (s, 1 H), 4.33 (t, 2 H), 4.00 (s, 3 H), 3.94 (t, 2 H), 3.74m, 2 H), 3.59 (m, 2 H), 3.40 (s, 3 H). HRMS (EI) Calcd. for CL7H2005S : 336.1031. Found: 336.1027

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ATHEROGENICS, INC.; WO2004/56727; (2004); A2;,
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Application of 1663-61-2, A common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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.

A mixture of intermediate 2 (4 g, 15 mmol), acetic anhydride(5.8 g, 56.9 mmol), and triethyl orthobenzoate (10.1 g, 45 mmol)in toluene (25 mL) was stirred for 5 h at 110 C. After that time,the solvent was concentrated. The precipitate was filtered off,and dried to give 3 as a yellow solid (4.56 g, 76percent). 1H NMR(400 MHz, DMSO-d6) d 8.75 (d, J = 1.3 Hz, 1H), 8.11 (d, J = 8.1 Hz,1H), 7.93 (dd, J = 8.1, 1.6 Hz, 1H), 7.61?7.55 (m, 3H), 7.51 (dd,J = 7.7, 1.8 Hz, 2H), 4.86 (s, 2H), 4.03 (m, 2H), 3.89 (s, 3H), 1.36(t, J = 7.0 Hz, 3H). ESI-MS m/z: 400.0 [M+H]+.

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Yan, Shuang; Wang, Lei; Zhang, Haotian; Tian, Ye; Zhao, Yanfang; Gong, Ping; Bioorganic and Medicinal Chemistry; vol. 25; 6; (2017); p. 1778 – 1786;,
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Related Products of 17715-69-4, A common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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: A suspension of Pd2(dba)3 (6.9 mg, 0.0075 mmol), tBu3PHBF4 (8.7 mg,0.03 mmol), KOH (42 mg, 0.75 mmol), aryl bromide 9 (0.36 mmol) and tetralone 10(0.3 mmol) in a mixture of dioxane/water (4:1, v/v, 3 mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100 ¡ãC, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4,filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography.

The synthetic route of 17715-69-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Manvar, Dinesh; Fernandes, Talita De A.; Domingos, Jorge L.O.; Baljinnyam, Erdenechimeg; Basu, Amartya; Junior, Eurides F.T.; Costa, Paulo R.R.; Kaushik-Basu, Neerja; European Journal of Medicinal Chemistry; vol. 93; (2015); p. 51 – 54;,
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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. 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Product Details of 887581-09-1

General procedure: A 25 mL Schlenk tube wascharged with a magnetic stirrer and DMSO (2.0 mL). Substituted(2-bromophenyl)methylamine (1) (0.5 mmol), amidine hydrochloride (2) (1.0 mmol),CuBr (0.1 mmol, 14.2 mg), and K2CO3 (1.5 mmol, 207 mg) were added to the tube.The mixture was stirred at 80-120 oC under nitrogen atmosphere for 24 h, and thenunder air for 0.5 h. The resulting mixture was cooled to room temperature and filtered,and the solid was washed with ethyl acetate for two times (3 ¡Á 3 mL). The combinedfiltrate was concentrated by the rotary evaporator, and the residue was purified bycolumn chromatography on silica gel using petroleum ether/ ethyl acetate as eluent togive the desired target product.

The synthetic route of 887581-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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Reference of 4393-09-3, 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. 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Epoxide (0.5 mmol) was dissolved in absolute ethanol (10 mL), mixed with amine (1.1 mmol), heated to reflux (78C) overnight. If amine HCl salt, add DiPEA (1.1 mmol). If using microwave conditions, substitute isopropyl alcohol for solvent and microwave, 120C, 15 min. Note- Use ammonium hydroxide (conc., 9 eq) for unsubstituted amine addition.

The chemical industry reduces the impact on the environment during synthesis (2,3-Dimethoxyphenyl)methanamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ross, Tina Morgan; Battista, Kathleen; Bignan, Gilles C.; Brenneman, Doug E.; Connolly, Peter J.; Liu, Jingchun; Middleton, Steven A.; Orsini, Michael; Reitz, Allen B.; Rosenthal, Dan I.; Scott, Malcolm K.; Vaidya, Anil H.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 3; (2015); p. 602 – 606;,
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Electric Literature of 101-55-3, These common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, 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.

The 10.0g (42.8mmol) 4- polybrominated diphenyl ethers dissolved in 100ml of tetrahydrofuran, cooled to -20 , dropping19.2ml (48.0mmol) of n-butyllithium, the reaction was kept 1 hour after dropwise. Then dropping 6.4g (36.0mmol)A compound of formula 3 was dissolved in 30ml of tetrahydrofuran, warmed to 0 deg.] C After the addition, the reaction was continued for 1 hour.Was added dropwise 50ml of saturated ammonium chloride solution, the organic phase was separated. The organic phase was concentrated to give a yellow solid 10.8g,Yield 86.4%.

Statistics shows that 1-Bromo-4-phenoxybenzene is playing an increasingly important role. we look forward to future research findings about 101-55-3.

Reference:
Patent; Okuura Dayton (Shanghai) Pharmaceutical Co., Ltd.; Yu, Libing; Guo, Maojun; Yang, Qingang; Ren, Huasen; (19 pag.)CN105622613; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 29578-39-0, Formula: C7H6BrFO

To a solution of 1-bromo-3-fluoro-5-methoxybenzene (15 g, 73.16 mmol), tris(2-methylphenyl)phosphane (1.781 g, 5.85 mmol) and ethyl acrylate (11.90 mL, 109.74 mmol) in TEA (135 mL) was added palladium(II) acetate (0.329 g, 1.46 mmol) under nitrogen gas atmosphere at room temperature, and the mixture was stirred at 90C for 2 days. The solvent was evaporated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give ethyl (E)-3-(3-fluoro-5-methoxyphenyl)acrylate (14.2 g, 63.3 mmol, 87%) as a colorless oil.

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:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; YAMAMOTO, SATOSHI; SHIRAI, JUNYA; WATANABE, HIROYUKI; FUKUMOTO, SHOJI; ODA, TSUNEO; TOKUHARA, HIDEKAZU; TOMATA, YOSHIHIDE; ISHII, NAOKI; TAWADA, MICHIKO; KOUNO, MITSUNORI; OCHIDA, ATSUKO; IMADA, TAKASHI; FUKASE, YOSHIYUKI; YUKAWA, TOMOYA; (719 pag.)TW2016/2105; (2016); A;,
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