Tag: M.W=200-300

Application of 17061-62-0, 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. 17061-62-0, name is Bis(4-methoxybenzyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of bis(4-methoxybenzyl)amine 30.1 (900 g, 3.49 mol, 1 eq) in DCM (9 L) was added TEA (634 mL, 4.55 mol, 1.3 eq) followed by dropwise addition of ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the ethanesulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. The reaction was quenched by the addition of water (4 L) to the reaction mixture. The layers were separated and the aqueous layer extracted with DCM (2x 2 L). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was adsorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10-80% EtOAc in hexanes) to provide the title compound 30.0 (1125 g, 3.22 mol, 92%) as white solid. 1H- NMR (400 MHz, CDC13) oe 7.23 (dd,J= 2.08, 6.62 Hz, 4H), 6.90 (dd,J= 2.12, 6.60 Hz, 4H), 4.29 (s, 4H), 3.83 (app s, 6H), 2.92 (q,J= 7.40 Hz, 2H), 1.33 (t,J= 7.40 Hz, 3H). GC-MS (ESI pos. ion) m/z: = 372.2 (M+Na).

The synthetic route of Bis(4-methoxybenzyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 261762-35-0, name is 5-Bromo-1,2-difluoro-3-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 261762-35-0, Computed Properties of C7H5BrF2O

To a mixture of 6-methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine (500 mg, 3.04 mmol) and 5-bromo-2,3-difluoroanisole (883 mg, 3.96 mmol) in dioxane (8 mL) was added t-BuONa (438 mg, 4.56 mmol), Pd2(dba)3 (40 mg, 0.04 mmol) and Ruphos (30 mg, 0.06 mmol) under N2. After being heated with stirring at 100 C for 12 hrs, the resulting reaction mixture was filtered. Thefiltrate was concentrated in vacuo, diluted with DCM (100 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column to give 2- (3 ,4-difluoro-5-methoxy-phenyl)-6-methoxy-3 ,4-dihydro- 1H- 2,7-naphthyridine (560 mg) as a gray 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:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H9BrO

In a four-necked flask equipped with a thermometer, reflux condenser, stirrer, and nitrogen introduction tube,Add 200g of N-methylpyrrolidone and 15.0g (0.11mol) of acetanilide, stir to dissolve acetanilide in N-methylpyrrolidonein.Add 22g (0.12mol) of 30wt% sodium methoxide and gradually heat to 100 C to distill off methanol to prepare acetanilide sodium salt solution.Add 20.2 g (0.1 mol) 4-bromo-3-methylanisole to the reaction bottle at 20 C for 30 minutes,Control the temperature of the material ? 40 , after the addition is complete, continue to stir the reaction at 40 for 45 minutes.15g of methanol was added, and the temperature was raised to 100 C within 30 minutes, and the low-boiling fraction was distilled off. Then, the reaction was continued at 100 C for 30 minutes.Finally, under vacuum conditions, the temperature is controlled within the range of 110-130 C, and N-methylpyrrolidone is distilled off,A reaction mixture containing the target product 4-methoxy-2-methyldiphenylamine was obtained. Add 200 g of water to the reaction mixture containing 4-methoxy-2-methyldiphenylamine and stir well,Dissolve soluble materials and filter to obtain crude 4-methoxy-2-methyldiphenylamine.The crude 4-methoxy-2-methyldiphenylamine is post-treated by methanol recrystallization, centrifugal separation, drying, etc.Obtained target product 4-methoxy-2-methyldiphenylamine 20.5g, purity 99.3%(Gas chromatography analysis),The reaction yield was 95.3% (based on 4-bromo-3-methylanisole).

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; Shandong Dao Ke Chemical Co., Ltd.; Shandong Morui Technology Co., Ltd.; Li Mingxin; Lu Fengyang; Wang Jiahui; Yang Shuren; Li Mingjing; Yan Xue; (13 pag.)CN104628585; (2016); B;,
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Electric Literature of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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 RBF was charged with (1,5-cyclooctadiene)(methoxy)-iridium(i) dimer (0.049 g, 0.075 mmol), 4,4′-di-tert-butyl-2,2′-dipyridyl (0.040 g, 0.149 mmol), and bis(pinacolato)diboron (1.339 g, 5.27 mmol). The flask was flushed with Ar (g), then hexane (15.30 ml) was added. A reflux condenser was attached to the flask, and the flask was heated to 50 C. for 10 minutes. 2-bromo-4-methoxy-1-methylbenzene (2.0 g, 9.95 mmol) was added and the reaction was stirred overnight at 50 C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-50% EtOAc:Heptane) to afford 2-(4-bromo-2-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.694 g, 2.122 mmol, 21.33% yield) as an off-white oily solid. m/z (ESI) 329.1 (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 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
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Some common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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. name: 1,3-Dibromo-2,2-dimethoxypropane

To a suspension of NaH (4.1 g, 100 mmol) (60% in mineral oil) in DMF (100 mL) was added 2-(4-bromophenyl)acetonitrile (10 g, 51 mmol) followed by l,3-dibromo-2,2-dimethoxypropane (11 g, 42 mmol). The reaction mixture was heated to 60 C for 12 h. After 12 h the reaction mixture was diluted with water (1000 mL) and washed with EtOAc (400 mLx2). The combined organics were washed with brine (100 mL), dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica (petroleum ether : EtOAc = 50: 1 to 20: 1) to afford 1-(4-bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile. MS (ESI) Calc’d [M+H]+, 296; found, 296.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22094-18-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCGOWAN, Meredeth Ann; ACHAB, Abdelghani; FRADERA, Xavier; HAN, Yongxin; LI, Derun; LIM, Jongwon; LIU, Kun; SCIAMMETTA, Nunzio; WHITE, Catherine, M.; YU, Wensheng; ZHANG, Hongjun; ZHOU, Hua; (109 pag.)WO2019/74747; (2019); A1;,
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Related Products of 35822-58-3, 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 35822-58-3 as follows.

General procedure: One equiv. of protected hydrazine was dissolved/suspended in EtOH containing 10% water (approx. 5 ml per 1 mmol of protected hydrazine), 1.05 eq of benzaldehyde acetal was added, followed by the addition of 0.05 equiv. of TsOH in an ethanolic solution (10 mg of TsOH per 0.5 ml of EtOH). The obtained reaction mixture was refluxed and monitored by TLC (silica gel) until full conversion of the starting material was observed. Ethyl acetate/light petroleum mixtures or pure ethyl acetate were used as TLC eluents. After completion of the reaction the solvent was removed under reduced pressure, approx. 15 ml of toluene was added to the residue and the solvent was again removed under reduced pressure. The obtained crude hydrazone was dissolved in commercial stabilized THF (approx. 4 ml per 1mmol of hydrazone), the flask was flushed with argon and 3 equiv. of 1M BH3-THF complex was added at room temperature, followed by 3 hours of stirring. The progress of the reaction was checked by TLC and if some unreacted hydrazone was left, stirring was continued for an additional 45 min. After thefull conversion of hydrazone EtOH (10 ml) was added to the reaction mixture (Caution: Liberation of hydrogen) and the obtained mixture was refluxed for 1 hour. After cooling to room temperature the solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution, water and saturated NaCl solution. The aqueous phase was extracted twice with ethyl acetate, the extracts were washed with saturated NaCl solution, combined with the organic phase, dried over anhydrous Na2SO4 and evaporated to dryness. The residue was purified by column chromatography on silica gel by using ethyl acetate/light petroleum 1:1 or 1:2 mixtures or pure ethyl acetate as eluent. For the exact information about the eluent used for monitoring reaction progress and chromatographic purifications, see the Rf value for each compound.

According to the analysis of related databases, 35822-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mastitski, Anton; Niinepuu, Siret; Haljasorg, Toiv; Jaerv, Jaak; Organic Preparations and Procedures International; vol. 50; 4; (2018); p. 416 – 423;,
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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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H20O3

General procedure: Triethyl orthoformate, orthoacetate, orthopropionate or orthobenzoate(10 mmol) was added dropwise to the mixture of 1,2,4,5-tetrazine-3,6-dicarbohydrazide (6) (0.5 g, 2.5 mmol), Lawesson’s reagent(1.12 g, (2.77 mmol) and glacial acetic acid (7 mL). The reaction wascarried out using conventional heating or microwave irradiation(150 W) in five cycles of 90 s with 2 min intervals at the temperature50-100 C.

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

Reference:
Article; K?dzia, Anna; Kudelko, Agnieszka; ?wi?tkowski, Marcin; Kruszy?ski, Rafa?; Dyes and Pigments; vol. 172; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 6876-00-2, name is 1-Bromo-3-phenoxybenzene, 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 6876-00-2, Product Details of 6876-00-2

STEP A 1-(m-phenoxy-phenyl)-2,2,2-trifluoro-ethanone A few drops of m-phenoxy-bromobenzene were added to a mixture of 16.6 g of magnesium (50% turnings) in 53 ml of tetrahydrofuran and the mixture was heated to 40-45 C. Crystallization began and the rest of 62.2 g of m-phenoxy-bromobenzene was added dropwise at reflux over 45 minutes. 183 ml of tetrahydrofuran were added and the mixture was refluxed for one hour and was cooled to 0 C. to obtain a solution of a magnesium compound. The said solution was then added at 0 C. over 40 minutes to a mixture of 40.8 g of sodium trifluoroacetate in 240 ml of tetrahydrofuran and the mixture was stirred for two hours and was poured into aqueous 0.1N hydrochloric acid solution. The mixture was extracted with ether and the ether phase was washed with water, with aqueous N sodium hydroxide and with water. The ether phase was added to two liters of methylene chloride and the mixture was evaporated to dryness under reduced pressure to obtain 56.2 g of raw 1-(m-phenoxy-phenyl)-2,2,2-trifluoro-ethanone which was used as is for the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-phenoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Roussel Uclaf; US4833163; (1989); A;,
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Synthetic Route of 103291-07-2, 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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-bromo-1-fluoro-2-methoxybenzene (Aldrich) (20 g, 97.5 mmol), methyl methacrylate (Aldrich) (24 g, 244 mmol) in DMF (150 ml) was added Pd(OAc)2 (2.2 g, 9.7 mmol), Bu3N (45 g, 244 mmol), TOP (8.9 g, 29 mmol). The resulting mixture was degassed and charged with N2 three times, and then stirred at 100 C. for 5 hrs. After cooling down, the mixture was filtered over celite. The filtration was evaporated under reduced pressure to the residue, which was treated with water and ethyl acetate. The separated organic layer was washed with brine (*3), dried over anhydrous Na2SO4 and filtered. The filtration was concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel eluting with 0?10% ethyl acetate in hexanes to afford the title compound as a yellow solid. LC-MS: Rt=1.48 mins; MS m/z [M+H]+ 225.0; Method 5-95AB 1.5minLC_v003

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-1-fluoro-2-methoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; CHEN, Shuhui; HE, Haiyang; LAGU, Bharat; QIN, Hua; WU, Chengde; XIAO, Yisong; US2015/183802; (2015); A1;,
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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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 27060-75-9

This experiment was carried out four times. Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-ylacetate (187 g, 1.87 mol), palladium(ll) acetate (7.5 g, 33 mmol) and tri-otolylphosphine (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 00 for 18 hours. After it had cooled to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 00. The resulting mixture was diluted with toluene (500 mL) and filtered through diatomaceousearth; the filter pad was thoroughly washed with ethyl acetate (2 x 1.5 L). The organic layer from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield:602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H]. 1H NMR (400 MHz, CDCI3) oe 7.05 (d,J=8.3 Hz, 1H), 6.70-6.77 (m, 2H), 3.79 (5, 3H), 3.65 (5, 2H), 2.22 (5, 3H), 2.14 (5, 3H).

The synthetic route of 27060-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (2015); A1;,
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