Author: Jessica.F

Electric Literature of 321-28-8, 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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 3-fluoro-4-methoxybromobenzene Into a flask of 5 l were charged 384 g (3.04 mol) of 2-fluoroanisole and 2.5 l of chloroform, to which was added dropwise 504 g (3.16 mol) of bromine over about 3 hours while cooling on an ice water bath at 10 C. The resulting mixture was stirred at room temperature over a night and heated under reflux for 8 hours. After the air cooling, the product was added with 1 l of water and 50 g of sodium bisulfite and sufficiently shaken to separate into two layers. The resulting organic layer was washed with an aqueous solution of 5% sodium hydrogen carbonate and further with 1 l of water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and distilled under a reduced pressure (4 mmHg, bp: 93-96 C.) to obtain 585 g (yield: 94%) of 3-fluoro-4-methoxybromobenzene.

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, 1-Fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nippon Mining Co., Ltd.; US5098602; (1992); A;,
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Synthetic Route of 162705-07-9, 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 162705-07-9 as follows.

General procedure: DCC (0.47 mmol, 1.2 eq.); the N-Fmoc-protected amino acid (0.472 mmol, 1.2 eq) and HOBt·H2O (0.47 mmol, 1.2 eq) were added to a solution of the 30-aminocombretastatin (0.39 mmol, 1 eq) in anhydrous DMF (1.3 mL). The reaction mixture was stirred under N2 atmosphere for 16 h. Then, it was ltered, and the ltrate was poured into a saturated aqueous NH4Cl solution and then extracted with AcOEt (3×15 mL). The combined organic extracts were washed 2 times with water and brine and dried over anhydrous MgSO4. After ltration and evaporation of the solvent under reduced pressure, the resulting residue was chromatographed on silica gel with Hexanes-AcOEt (6:4) to aord the corresponding N-Fmoc-protected derivatives 7 and 9.

According to the analysis of related databases, 162705-07-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Agut, Rauel; Alberto Marco, J.; Carda, Miguel; Falomir, Eva; Gil-Edo, Raquel; Martin-Beltran, Celia; Murga, Juan; Pla, Alberto; Molecules; vol. 25; 3; (2020);,
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Electric Literature of 6876-00-2, 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 6876-00-2 as follows.

EXAMPLE 29 1-(2-Fluoro-3-(3-phenoxyphenyl)prop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl) cyclopropane The method of Example 25 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.26 g), tetrahydrofuran (2 ml) and magnesium (22 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl)cyclopropane (Example 21) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C8; solvent: methanol; flow rate: 2 ml/min) to afford 1-(2-fluoro-3-(3-phenoxyphenyl) prop-1-enyl)-1-(2-fluoro-4-trifluoromethylphenyl)cyclopropane (38 mg, 27%).

According to the analysis of related databases, 6876-00-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; British Technology Group Limited; US5763700; (1998); A;,
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Synthetic Route of 89282-70-2, A common heterocyclic compound, 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, molecular formula is C5H13NO, 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.

[0407] In Examples, a room temperature usually indicates10 to 30 C. ?H NMR indicates a proton nuclear magnetic resonance spectrum, and chemical shift (6) is expressed in ppm, using tetramethylsilane as an internal standard substance.; [0424] The intermediate compound (1) (0.24 g, 1.0 mmol), 2-methoxy-2-methylpropylamine (0.13 g, 1.2 mmol), and HOST (0.01 g, 0.1 mmol) were added to chloroform (Amylene-added product) (2.5 mE). Afier EDCD (0.24 g, 1.2 mmol) was added to the mixed liquid at room temperature, the mixture was stirred at room temperature for 3 hours. Thereafier, dilute hydrochloric acid was added to the reaction mixture, followed by extraction with chloroform two times. After the organic layer was passed through a short column to remove impurities, this was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.24 g of a compound offollowing formula: (hereinafier, referred to as compound (8)).; [0425] ?H-NMR (CDC13, TMS, oe(ppm)): 1.21 (6H, s),3.23 (3H, s), 3.46 (2H, d), 4.61 (2H, s), 4.65 (2H, s), 6.73(1H, s), 7.10 (1H, br s), 7.30-7.40 (5H, m)

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; SUMITOMO CHEMICAL COMPANY, LIMITED; MITSUDERA, Hiromasa; OKAJIMA, Mayumi; KOWATA, Ayano; AWASAGUCHI, Kenichiro; UJIHARA, Kazuya; (108 pag.)US2017/295789; (2017); A1;,
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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. 123652-95-9, name is (3-Fluoro-4-methoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Formula: C8H10FNO

General procedure: A microvawe vial (ovendried and under argon) was chargedwith the corresponding bromoindazole derivative (1.0 equiv.), theappropriate amine (1.2 equiv.), Pd(OAc)2 (5 mol%), BrettPhos(10 mol%), Cs2CO3 (1.5 equiv.) and anhydrous dioxane (0.2 mmol/mL). The vial was capped properly, flushed with argon and heatedto 120 C overnight. After cooling, the reaction mixture wasconcentrated under vacuum. The crude residue was diluted withwater and the aqueous phase was extracted 3 times with EtOAc.The organic layers were combined, washed with brine, dried overNa2SO4, filtered, concentrated and purified by silica gel columnchromatography, using the appropriate heptanes:EtOAc mixture.

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; Bollenbach, Maud; Lugnier, Claire; Kremer, Melanie; Salvat, Eric; Megat, Salim; Bihel, Frederic; Bourguignon, Jean-Jacques; Barrot, Michel; Schmitt, Martine; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 269 – 290;,
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Adding a certain compound to certain chemical reactions, such as: 34967-24-3, name is 3,5-Dimethoxybenzyl amine, 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 34967-24-3, Recommanded Product: 34967-24-3

To a stirred solution of 2,4 dichloro-pyrido [2,3-d] pyrimidine (1.3 g, 6.7 mmol) and 3, 5-dimethoxybenzylamine (1.1 g, 6.7 mmol) in 30 mL EtOH at RT was added TEA (4 mL, 28.7 mmol). A precipitate formed that was filtered off and washed with cold EtOH followed by hexanes to give 1.8 g of the title compound (82%) as a solid. mp 185C (dec).’H-NMR (DMSO-d6) 8 : 9.5 (t, 1H), 8. 9 (dd, 1H), 8.7 (dd, 1H), 7.5 (m, 1H), 6.5 (d, 2H), 6.4 (t, 1H), 4.6 (d, 2H), 3.7 (s, 6H). MS (m/z, %): 331 (100).

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; PFIZER PRODUCTS INC.; WO2005/61497; (2005); A1;,
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Related Products of 168268-00-6, 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. 168268-00-6, name is 4-(Benzyloxy)-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of 4-(benzyloxy)-3-fluoroaniline (1.04 g, 4.8 mmol) (WO 2005030140) under a nitrogen atmosphere was added acetic acid (2.3 ml_, 38.3 mmol), triethy lorthoformate (2.44 ml_, 14.4 mmol) and sodium azide (0.34 g, 5.3 mmol), and the reaction mixture heated at 95 C for 2.5 hours. The solution was then allowed to cool to room temperature, and water was added followed by extraction with ethyl acetate three times. The extracts were combined and washed with brine and dried over magnesium sulfate. The mixture was filtered and concentrated under reduced pressure, and the crude material purified by chromatography on silicon gel (20 – 40 % ethyl acetate in heptane) to give the title compound as a white solid (1.12 g, 86 %). 1H NMR (400 MHz, deuteromethanol) delta 9.65 (s, 1 H), 7.73 – 7.68 (dd, 1 H, J=1 1 , 2.5 Hz), 7.60 – 7.57 (m, 1 H) 7.47 – 7.45 (m, 2H), 7.40 – 7.30 (m, 5H), 5.24 (s, 2H); LCMS (ES+): 271 .1 (M+1 ).

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

Reference:
Patent; PFIZER INC.; MASCITTI, Vincent; MCCLURE, Kim Francis; MUNCHHOF, Michael John; ROBINSON, Ralph Pelton, Jr.; WO2012/69948; (2012); A1;,
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Reference of 171290-52-1, 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. 171290-52-1 name is 3,5-Dimethoxyphenylacetylene, 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.

General procedure: The azido derivative of N,-C terminal protected L-serine (1.0equiv) was taken in a 5:1 dry THF and water mixture solvent anddegassed it for 5 min with nitrogen gas. Then, terminal alkyne(1.1 equiv) was added with continuing stirring and degassing forthe next 5 min. Then 6 mol% sodium ascorbate and 1 mol% powderCuSO4 were added. The reaction mixture was degassed and allowed to proceed 18-20 h about 65-70 C. After total consumptionof the starting azide, the reaction mixture evaporatedcompletely and work up done by EtOAc and NH4Cl solution. Theorganic layer was washed with brine, dried over Na2SO4. Thesynthesized trizolyl amino acids were separated by column chromatography(si-gel, PE/EA = 1:1) and characterized. The averageyields were 50-85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethoxyphenylacetylene, and friends who are interested can also refer to it.

Reference:
Article; Bag, Subhendu Sekhar; Jana, Subhashis; Pradhan, Manoj Kumar; Bioorganic and Medicinal Chemistry; vol. 24; 16; (2016); p. 3579 – 3595;,
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Synthetic Route of 20781-20-8, 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 20781-20-8 as follows.

A mixture of 3-hydroxyphthalic anhydride (1.24 g, 7.6 mmol), 2,4-dimethoxybenzylamine (1.14 mL, 7.6 mmol) and acetic acid (5 mL) was heated at 80C for 24 hours. The mixture was allowed to cool and diluted with water (20 mL). The white solid was collected by filtration, washed well with water and dried to give the title compound (1.73 g, 73%). 1H NMR (DMSOd6) 11.00 (1 H, s), 7.62 (1 H, dd), 7.29 (1 H, d), 7.21 (1 H, d), 6.90 (1 H, d), 6.56 (1 H, d), 6.43 (1 H, dd), 4.59 (2H, S)1 3.79 (3H, s), 3.72 (3H, s). MS: [M-H+] 314.

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
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Synthetic Route of 887581-09-1,Some common heterocyclic compound, 887581-09-1, name is (2-Bromo-5-methoxyphenyl)methanamine, molecular formula is C8H10BrNO, 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 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 × 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.

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-5-methoxyphenyl)methanamine, its application will become more common.

Reference:
Article; Liu, Qing; Zhao, Yufen; Fu, Hua; Cheng, Changmei; Synlett; vol. 24; 16; (2013); p. 2089 – 2094;,
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