Tag: M.W=200-300

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. 458-50-4, name is 4-Bromo-3-fluoroanisole, A new synthetic method of this compound is introduced below., Formula: C7H6BrFO

A mixture of 4-bromo-3-fluoro anisole (2.0 g, 9.75 mmol), methyl 3-methyl-4-(4,4,5,5- tetramethyl-1-3s2-dioxaborolan-2-yl)benzoate (2.8 g, 10.14 mmol), Cs2C03 (6.99 g, 21.46 mmol) and catalytic amount of Pd(PPh3)4 (1.13 g, 0.975 mmol) in dioxane (50 mL) was stirred at 80 °C overnight. The solvent was removed. Water was added. The mixture was extracted with CH2C12 (3 x 20 mL). Washed with brine and dried over Na2SC>4.The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (1:9) to give the title compound as a colorless solid.

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; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (2012); A1;,
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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. Recommanded Product: 22094-18-4

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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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, Quality Control of 5-Bromo-1,2-difluoro-3-methoxybenzene

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.

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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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Synthetic Route 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 27060-75-9

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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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. 4463-59-6, name is 1-(2-Bromoethoxy)-2-methoxybenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-(2-Bromoethoxy)-2-methoxybenzene

36 g(0.156 ml) of 2-(methoxyphenoxy)ethylbromide and 27.3 grams (0.186 mole) of phthalimide are dissolved in 100 ml of dimethylacetamide, and stirred with heat for diffusion to 90 C. After 30 minutes, 10.45 g(0.186 mole) of potassium hydroxide is dissolved in 30 ml of methanol solution for heating and diffusing over 1.5 hours. Upon cooling, the mixed solution is poured into 300 ml of water. After filtrating the extracted solids, 200 ml of 10% potassium carbonate solution is added, and stirred with heat. The paste-like substance obtained is filtrated. After rinsing with tap water several times, moisture-free alcohol is used for re-crystallization until while crystallization is obtained. 21 grams(0.071 mole) of the above product and 3.55 grams (0.071 mole) of hydrazine hydrate are dissolved in 70 ml of moisture-free alcohol, and upon heating and diffusing for 45 minutes, 20 ml of 18% hydrochloric acid is added into the mixture to continue the diffusion for one hour before cooling. After filtration, the residue obtained from reduction is mixed with 20% of sodium hydroxide for alkalization. Chloroform is used for extraction, and upon filtration and pressurized reduction, it is filled into the silicone tube for separation, while using ethyl acetate as the diluent to obtain an oily product, i.e. 2-(2-methoxy-phenoxy)ethylamine.

The synthetic route of 4463-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chen, Ing-Jun; US2001/56211; (2001); A1;,
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Electric Literature of 22094-18-4, A common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, molecular formula is C5H10Br2O2, 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.

Example 129A 3,3-dimethoxy-1-[4-(trifluoromethoxy)phenyl]cyclobutanecarboxamide 2-[4-(Trifluoromethoxy)phenyl]acetonitrile (7.86 mL, 50 mmol), 1,3-dibromo-2,2-dimethoxypropane (13.10 g, 50.0 mmol), and sodium tert-butoxide (10.57 g, 110 mmol) were dissolved in DMSO (100 mL) and water (5 mL), and the mixture was heated for 1 hour at 125 C. The reaction was cooled to ambient temperature and stirred overnight. The reaction mixture was diluted with water and extracted three times with diethyl ether. The combined organic layers were washed with brine, dried with MgSO4, filtered, and concentrated to give the title compound (17.02 g, 53.3 mmol, 107% yield). MS (DCI+): m/z 320.1 (M+H), 337.1 (M+NH4). 1FINMR (300 MHz, DMSO-d6) delta 7.44 (d, J=8.8 Hz, 2H), 7.34 (s, 1H), 7.31 (d, J=8.8 Hz, 2H), 6.90 (s, 1H), 3.05 (s, 3H), 3.02-2.93 (m, 5H), 2.41 (d, J=13.4 Hz, 2H).

The synthetic route of 22094-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2014/80803; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)benzene, 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 1663-61-2, Safety of (Triethoxymethyl)benzene

b. 1-Azidoethyl-2,4-dibenzoylmannose To a 1.0 L, 3-neck flask containing a stir bar, nitrogen inlet and 300 mL of anhydrous acetonitrile was added 25 gm 1-azidoethylmannose (100.4 mmole), and 50 mL triethyl orthobenzoate (220 mmole, 2.2 equiv.). The resulting slurry was stirred at room temperature and 0.8 mL (10 mmole) trifluoroacetic acid (TFA) was added neat. The solution cleared within 10 minutes and stirring was continued for an additional two hours, then 25 mL of 10percent aqueous TFA was added and stirring was continued for an additional 2 hours to hydrolyze the intermediate to the ester isomers. The solvent was evaporated under vacuum to a viscous oil, which was triturated with 50 mL DCM and again evaporated to a viscous oil. Toluene (70 mL) was added to the residue and the viscous solution was seeded with 2,4-dibenzoylazidoethylmannose. A fine precipitate formed within 15 minutes and stirring was continued overnight at room temperature. The resulting heavy suspension was set in the freezer for 2-4 hours, then filtered and the solid washed with ice cold toluene (2*10 mL). The solid was air dried to a constant weight to give 21 gm (TY 22.85 gm 50percent isomeric purity) of ?95percent isomeric purity. The product was taken into 40 mL toluene, stirred for 1 hour and then set in the freezer for an additional 2 hours. The solid was filtered and washed (2*10 mL) with ice cold toluene and air dried to a constant weight to give 18.5 gm of the single isomer product 2,4-dibenzoylazidoethylmannose in 83percent yield. The mother liquors contained the undesired isomer and a small amount of the desired isomer. The reaction was monitored by TLC: SG (Hexane/Ethyl Acetate 7/3) Starting Material Rf 0.0, orthoester intermediate Rf 0.9. (Hexane/Ethyl Acetate: 8/2) SM Rf 0.8, desired isomer Rf 0.4, un-desired isomer Rf 0.2 1H NMR 300 MHz (CDCl3) delta 8.12 (t, 4H), 7.66 (t, 2H), 7.5 (m, 4H), 5.56 (t, 1H), 5.48 (m, 1H), 5.14 (m 1H), 4.5 (dd, 1H), 4.0 (m, 2H), 3.8 (m, 3H), 3.56 (m, 1H), 3.44 (m, 1H).

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; SMARTCELLS, INC.; Chen, Zhiyu; Lancaster, Thomas M.; Zion, Todd C.; US2013/190475; (2013); A1;,
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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. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of (2-Bromoethoxy)benzene

General procedure: Anhydrous K2CO3 (1.2 M equiv) was added to the solution of GA or compound 42 (0.2 mmol) and halogenating agents (1.2 M equiv) in dry DMF (5 mL). The reaction mixture was stirred at room temperature until the starting material was not observed by TLC. The mixture was treated with H2O (20 mL), the aqueous layer was extracted with EtOAc (2×20mL). The joined organic extracts were washed three times with H2O (60 mL) and saturated NaCl (60 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The residue was chromatographed using a silica gel column to afford the pure target products.

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry Letters; vol. 22; 10; (2012); p. 3473 – 3479;,
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Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, 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 17715-69-4, Product Details of 17715-69-4

General procedure: Synthesis of 4′-methoxybiphenyl-4-carbonitrile. A reaction vessel equipped with filtration frit was charged with polystyrene resin-bound benzyl(di-tert-butyl)phosphonium chloride (6.20 mg, 4% mol, 100-200 mesh resin containing 1.60 mmol/g phosphonium hydrochloride) and flushed with argon. Next, 5mL of degassed dioxane was added followed by 20 mL of diisopropylamine and reaction mixture was agitated for 1 h at room temperature. Subsequently, the solvent was removed and the resin washed with degassed dioxane (3×5 mL). The resin was resupended in dioxane (5.0 mL) and Pd2(dba)3·CHCl3 (5.20 mg, 2% mol) added and the reaction mixture was agitated for 12 h at room temperature. The Pd-doped resin becomes black in colour. The solvent was removed and catalyst washed with degassed dioxane (3×5 mL). 4-Bromobenzonitrile (45.5 mg, 0.25 mmol), 4-methoxyphenylboronic acid (42.0 mg, 0.28 mmol), Cs2CO3 (179.2 mg, 0.55 mmol), 5 mL of degassed dioxane were added and the suspension agitated for 72h at room temperature. The solution was filtered and the Pd-doped catalyst re-suspended and washed with degassed dioxane (3 x 5 mL). Evaporation of the combined dioxane extracts under vacuum and purification by chromatography on silica gel (ethyl acetate/hexane 1:9) afforded the title compound (41 mg, 80%). All entries reported in table 2 were conducted under the above conditions.

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Reference:
Article; Ullah, Ehsan; McNulty, James; Sliwinski, Marcin; Robertson, Al; Tetrahedron Letters; vol. 53; 31; (2012); p. 3990 – 3993;,
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