Author: Jessica.F

Related Products of 450-91-9, A common heterocyclic compound, 450-91-9, name is 4-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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.

iii: Intermediate 3 (1.0 eq) and cesium carbonate (2.0 eq) and corresponding phenylamine (1.2 eq) were added into a dry reaction flask. Dry DMF was used as reaction solvent, N2 was used to remove water vapor and oxygen. Then catalyst and ligand Pd(AcO)2 (0.1 eq) and Xantphos (0.1 eq) were added. The reaction mixture was transferred to a 60 C oil bath, 6~7 hours. After the reaction completed, the mixture was filtered and evaporated. Intermediate 4 was gained. The yield was 50%.

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:
Article; Rong, Juan; Feng, Zhan-Zhan; Shi, Yao-Jie; Ren, Jing; Xu, Ying; Wang, Ning-Yu; Xue, Qiang; Liu, Kun-Lin; Zhou, Shu-Yan; Wei, Wei; Yu, Luo-Ting; Bioorganic and Medicinal Chemistry Letters; vol. 29; 19; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22483-09-6, 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. 22483-09-6, name is 2,2-Dimethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of isobenzofuran-i, 3-dione (80.Og, 0.540 mol) in toluene (1000 mL) added2, 2-dimethoxyethanamine (85.10 g, 0.811 mol), followed by N,N-diisopropylethylamine(0.187 mL, 1.080 mol) at room temperature. The reaction mixture was stirred at 120 C with dean stark apparatus for 16 h. After completion of the reaction, the reaction mixture was evaporated under reduced pressure. The residue obtained was diluted with in dichloromethane, filtered through pad of celite and dried over sodium sulfate and concentrated. The crude obtained was washed with petroleum ether to give the titled compound (100 g, 79%) as an off white solid. LCMS: m/z no ionization; ?H NMR (300 MHz, Chloroform-d) 7.89 – 7.81 (m, 2H), 7.76 – 7.68 (m, 2H), 4.77 (td, J = 5.8, 0.8 Hz, 1H), 3.82 (dd, J= 5.8, 0.8 Hz, 2H), 3.38 (d, J= 0.9 Hz, 6H).

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, 2,2-Dimethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1978-39-8, name is 5-Fluoro-2-methoxyaniline, A new synthetic method of this compound is introduced below., name: 5-Fluoro-2-methoxyaniline

To a THF (20 mL) solution of 5-fluoro-2-methoxyaniline (1.76 g), a THF (30 mL) solution of pyridinium bromide perbromide (4.36 g) was added dropwise under ice-cooling, and the reaction solution was agitated for 30 minutes at room temperature. The solid which deposited from the reaction mixture was separated by filtering and the solid was washed by THF. After the obtained solid was dissolved with water and ethyl acetate, the aqueous layer was neutralized with a saturated sodium bicarbonate water, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent:hexane-ethyl acetate system), and 1.83 mg of the title compound was obtained. 1H-NMR (CDCl3) delta (ppm): 3.82 (s, 3H), 3.91 (brs, 2H), 6.50 (d, J=9.6 Hz, 1H), 6.84 (d, J=6.0 Hz, 1H).

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; Eisai Co., Ltd.; US2006/4013; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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: NaN3 (0.42 g, 6.5 mmol) was added to a stirred solution of 1-bromo-4-(3-bromopropoxy)benzene (1.47 g, 5 mmol) in DMSO (25 mL). The mixture was stirred for 12 h at room temperature, diluted with H2O (50 mL), and extracted by EtOAc (50 mL .x. 3). The organic layer was separated, dried with Na2SO4, and concentrated under reduced pressure. The residue was white solid and reacted to the next step without further purification. The synthetic method for the compound 5b was similar to the synthesis of compound 5a.

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

Reference:
Article; Wang, Shengzheng; Jin, Gang; Wang, Wenya; Zhu, Lingjian; Zhang, Yongqiang; Dong, Guoqiang; Liu, Yang; Zhuang, Chunlin; Miao, Zhenyuan; Yao, Jianzhong; Zhang, Wannian; Sheng, Chunquan; European Journal of Medicinal Chemistry; vol. 53; (2012); p. 292 – 299;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 321-28-8,Some common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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.

Add 3-fluoroanisole (85.0g, 0.67mol), tetrahydrofuran (3540mL), tetramethylethylenediamine (78.3g, 0.67mol) at room temperature,Replace with nitrogen three times, turn on stirring,Cooled to -50 ~ -78 , was added dropwise a solution of sec-butyllithium (870mL, 1.3M), after the addition was complete stirring incubated 2 to 3 hours, a solution of N, N- dimethylformamide (67.5g, 0.92 mol), heat and stir for 1 hour,After the reaction was completed, a 13% acetic acid aqueous solution (1464 g) was added dropwise at -50 to -78 C, and the layers were separated. The aqueous phase was extracted with ethyl acetate (350 mL * 3), and the organic phases were combined.After washing with water (500mL), 1N hydrochloric acid,The organic phase is concentrated to no droplets,A pale yellow mixture was obtained and crystallized from methyl tert-butyl ether (150 mL) to give a white solid,Drying gave compound II (57.7 g, 57.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-2-methoxybenzene, its application will become more common.

Reference:
Patent; Shanghai Bopunuo Science And Technology Co., Ltd.; Guo Peng; Ji Changyou; Wang Jun; Zhang Dong; Liang Shoushan; Zhu Wenfeng; (15 pag.)CN110759870; (2020); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Methoxybenzene-1,2-diamine

4-Methoxy-2-trifluoromethyl-1H-benzimidazole The compound of Example 103 (6.49 g) was dissolved in trifluoroacetic acid (75.0 mL) under ice cooling, followed by stirring for 5 hours to heating under reflux. After evaporating the solvent, the residue was dissolved in ethyl acetate and poured into a saturated aqueous sodium hydrogen carbonate solution. The organic layer was collected by separation, washed with saturated brine, and then dried over anhydrous sodium sulfate. After evaporating the solvent, the resulting solid was suspended in hexane and collected by filtration to obtain the desired product (8.69 g) as a yellowish brown powder. 1H NMR (CD3OD, 400 MHz): delta 4.01 (3H, s), 6.89 (1H, d, J=8.0 Hz), 7.24 (1H, d, J=8.0 Hz), 7.32 (1H, dd, J=8.0, 8.0 Hz).

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 37466-89-0.

Reference:
Patent; Kyorin Pharmaceutical Co., Ltd.; EP2168959; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 29578-39-0, 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 29578-39-0 as follows.

A mixture of 1-bromo-3-fluoro-5-methoxy-benzene (80 g, 0.39 mol), TEA (118 g, 1.17 mol), Pd(OAc)2 (16 g, 20%) and DPPP (16 g, 20%) in MeOH (800 mL) is stirred under a 3 Mpa atmosphere of CO for 2 days. The mixture is filtered and the filtrate is concentrated under reduced pressure. The crude is purified by flash silica gel chromatography to afford compound D-9-1 (42 g, 59% yield).

According to the analysis of related databases, 29578-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 4393-09-3, 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. 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a typical reaction, the Wang resin (3, 2.0 g, 1.2 mmol/g, 100-200 mesh and 1% DVB) was swollen in CH2Cl2 (20 mL). 5-Bromopentanoic acid (4, 2.15 g, 12.0 mmol) and DIC (1.51 g, 12.0 mmol) were dissolved in the minimum volume of CH2Cl2/DMF (1:1) required for complete dissolution. The activated scaffold solution was added to the resin, followed by the addition of slurry of DMAP (4 mg, 10 mol %) in CH2Cl2 (0.5 mL). The reaction vessel was shaken at room temperature for 48 h. The resin was washed with CH2Cl2 (2 × 25 mL), DMF (2 × 25 mL), MeOH (2 × 25 mL) again followed by DMF (2 × 25 mL), CH2Cl2 (3 × 25 mL), and then further dried in vacuo overnight to afford the resin-bound 5-bromopentanoic acid in good yield (2.73 g, 81%). Next, to the resin-bound 5-bromopentanoic acid (2.70 g, 3.9 mmol), swelled in DMF (10 mL), K2CO3 (2.13 g, 15.6 mmol) was added at ambient temperature, and the reaction suspension was stirred for another 30 min. Later, methyl 2-azido-4-hydroxy-5-methoxybenzoate (5, 1.73 g, 7.8 mmol) was added to the resin. The reaction suspension was stirred at 50 C for 48 h. The solid-support was washed with water (3 × 20 mL), CH2Cl2 (2 × 20 mL), MeOH (3 × 15 mL), and then dried in vacuo to afford the resin-bound precursor 6a (3.07 g, 75%). To a suspension of this resin-bound ester in 1,4-dioxane (10 mL) was added 1 N NaOH solution (2.5 mL) and the reaction mixture was heated at 80 C for 12 h. On cooling, the resin was filtered and rinsed with water (2 × 15 mL), water/dioxane (1:9, 2 × 15 mL), MeOH (2 × 15 mL), CH2Cl2 (2 × 15 mL), Et2O (2 × 15 mL) and dried in vacuo to afford the resin-bound acid. Next, to the resin-bound 2-azido-4-(5-ethoxy-5-oxopentyloxy)-benzoic acid (2.81 g, 2.6 mmol) swelled in CH2Cl2 (10 mL), EDCI (0.99 g, 5.2 mmol), HOBt (0.71 g, 5.2 mmol) and l-proline methyl ester (7a, 0.84 g, 6.5 mmol) were added. This reaction mixture was stirred for 12 h at room temperature, then resin was filtered and washed with H2O (3 × 10 mL), CH2Cl2 (2 × 10 mL), MeOH (3 × 10 mL) and Et2O (3 × 10 mL) to afford the resin bound methyl 5-(5-azido-4-(2-formylpyrrolidine-1-carbonyl)-2-methoxyphenoxy) pentanoate 8a in good yield (2.89 g, 71%). To a suspension of this resin (0.110 g, 1.2 mmol) in CH2Cl2 (5 mL), AlCl3 (0.79 g, 6 mmol), NaI (0.22 g, 2 mmol) and 2-(4-methoxyphenyl)ethanamine (9a, 0.35 mL, 2.4 mmol) were added at room temperature and stirred for 6 h. Aqueous 1 M potassium carbonate solution (2 mL) was added to the reaction mixture followed by excess of NaI, quenched with saturated sodium thiosulfate (Na2S2O3), and then resin was separated by simple filtration and washed with CH2Cl2 (10 mL). The removal of excess amine impurities from the final resin cleaved crude product was achieved by solid-supported liquid-liquid extraction (SLE) with a fritted vessel previously packed with ?Varian?s Hydromatrix?. The crude compound 1a which contains excess of amine was passed through the Hydromatrix support into a collection plate below, while the amine salts were retained by the solid matrix, resulting in the effective removal of the amine impurities. This filtrate and washings were evaporated to dryness under reduced pressure. Finally, it was further purified by the preparative thin layer chromatography by using ethyl acetate:methanol (98:2) as eluent to afford the corresponding compound 1a in high purity (brown solid, 0.013 g, 56%).

The synthetic route of (2,3-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Prabhakar; Shankaraiah, Nagula; Markandeya, Nagula; Venkat Reddy; Srinivasulu, Vunnam; Sathish, Manda; Tetrahedron Letters; vol. 54; 33; (2013); p. 4435 – 4441;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, molecular formula is C7H5BrF2O, 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

To the reaction vessel of 3000 L was added the above-obtained 2,3-difluoro-5-bromoanisole and 215 kg of AlCl3,And then pumped into 1800L of toluene,Sealed reactor, heated to reflux after 5h sampling analysis,Raw materials have been basically complete.The material with nitrogen into the 5000L washing kettle,Pumped into 1000L water stirring washing, discard the water layer,And then repeated washing once a few layers into the distillation kettle,After the toluene was distilled off, it was distilled under reduced pressure to obtain 206.1 kg of 2,3-difluoro-5-bromophenol,The product content of GC was 99.4%.The recovered toluene can be reused after drying. The total yield of the two-step reaction was 82.2%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 261762-35-0, its application will become more common.

Reference:
Patent; Zhejiang Linjiang Chemical Industry Co., Ltd.; Yi, Miao; Yin, Xin; Chen, Huanjun; Wang, Qijin; Xu, Xin; (8 pag.)CN106478377; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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.

Copper iodide (54 mg, 0.283 mmol) and Tetrakis(triphenylphosphine) palladium (105 mg, 0.091 mmol) were added. Lastly 1-bromo-4-(difluoromethoxy)benzene (0.750 g, 3.36 mmol) was added, the vial was covered with a teflon septa, an aluminum cap was crimped in place, and the assembly was set on a Biotage Emrys microwave instrument to irradiate at 80 C. for 30 minutes. The crude reaction was diluted with diethylether, washed with saturated ammonium chloride, and purified via column chromatography on a Yamazen W-Prep 2XY using 25% EtOAc in hexanes. Concentration by rotary evaporation afforded 500 mg of oil (96%); 1H NMR (400 MHz, DMSO-d6) delta ppm 3.03 (t, J=4.6 Hz, 4H) 3.73 (t, J=4.6 Hz, 4H) 7.13-7.14 (m, 1H) 7.16 (d, J=2.6 Hz, 1H) 7.17-7.19 (m, 2H) 7.22 (d, J=8.8 Hz, 2H) 7.24 (t, J=73.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H); MS (ES) m/z 348.2 [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 1-Bromo-4-(difluoromethoxy)benzene, its application will become more common.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem