Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 17061-62-0, name is Bis(4-methoxybenzyl)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 17061-62-0, Application In Synthesis of Bis(4-methoxybenzyl)amine

To an ice-cooled solution of 361.01 (900 g, 3.49 mol) in DCM (9 L) was added TEA (634 mL, 4.55 mol) followed by ethanesulfonyl chloride (399 mL, 4.19 mol, 1.2 eq) dropwise. (Note: The internal temperature was kept between 5-10 C during the addition of the ethane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. Alter 1.5 h, TLC showed complete loss of starting material. The reaction was quenched with water (4 L), and the layers were separated. The aqueous layer was then extracted with more DCM (2 x 2 L). The combined organic layers were washed with brine (2 x 1 L), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was absorbed onto a plug of silica gel purified by silica gel chromatography (eluent: 10-80% EtOAc in hexanes) to provide 361.0 (1125 g, 92% yield) as a white solid. 1H-NMR (400 MHz, CDC13) oe 7.23 (dd,J=2.1, 6.6 Hz, 4H), 6.90 (dd,J2.1, 6.6 Hz, 4H),4.29 (s, 4H), 3.83 (s, 3H) 3.83 (s, 3H), 2.92 (q, J=7.4 Hz, 2H), 1.33 (t, J=7.4 Hz, 3H). LCMS-ESI (pos.) m/z: 372.2 (M+Na)t

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, Bis(4-methoxybenzyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; BROWN, Matthew; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HOUZE, Jonathan; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YEH, Wen-Chen; (815 pag.)WO2018/97944; (2018); A1;,
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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 1516-96-7 as follows. name: 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene

To a 300 mL pressure bottle was added 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (26 g, 87 mmol).Trimethyl ethynyl silicon (14.1 mL, 100 mmol), cuprous iodide (332 mg, 1.74 mmol),Triphenylphosphine palladium dichloride (611 mg, 0.87 mmol), triethylamine (60 mL),The mixture was reacted at 75 C for 12 h, cooled to room temperature, filtered and concentrated and applied directly to next.

According to the analysis of related databases, 1516-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Shi Shiliang; Cai Yuan; Yang Xintuo; Li Feng; (67 pag.)CN109776422; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, 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 14804-31-0, Recommanded Product: 14804-31-0

General procedure: 25-ml RB was charged with 4-iodo anisole (1.0 mmol), phenyl boronic acid (1.5 mmol), GO-PMMA-Pd catalyst (0.3 mol %), K2CO3 (1 mmol), TBAB (10 mol %) and 2 ml water. The mixture was allowed to stir at 90 C for an appropriate time (Table 1) and the extent of the reaction was monitored by thin layer chromatography (TLC). After the completion of the reaction, the reaction mixture was extracted by ethyl acetate (2¡Á25 mL) and washed with water repeatedly. The catalyst was filtered off and washed several times with ether and water (1:1) until no significant product was obtained in the wash. The recoverd catalyst was reused for the next coupling experiment. The reaction mixture was dried over anhydrous Na2SO4, concentrated in vacuum and purified by column chromatography on silica gel 60-120 mesh using petroleum ether as eluent to obtain pure product. The catalyst recoverd after 5th run was subjected to ICP-AES for Pd content analysis. The isolated products were analysed by 1H NMR and 13C NMR spectroscopy.

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, 4-Bromo-1-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Basak, Puja; Ghosh, Pranab; Synthetic Communications; vol. 48; 19; (2018); p. 2584 – 2599;,
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Synthetic Route of 57478-19-0, A common heterocyclic compound, 57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, molecular formula is C13H10F3NO, 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.

5-Nitro-N-para-[4-(trifluoromethyl)phenoxy]phenyl-isothiazole-3-carboxamide (58) To 0.8g (4.6mmol) of 5-nitro-isothiazole-3-carboxylic acid (prepared according to the method described in R. J. A. Walsh, K. R. H. Woolbridge, J. Chem. Soc. Perkin Trans 1, 1972,1247-1249) is added 14 ml of thionyl chloride under nitrogen, and the resulting mixture is stirred at reflux for 3 hours. After cooling, the solvent is evaporated to give a solid. This solid is suspended in a mixture of 20ml of diethyl ether and 20ml of dichloromethane. The suspension is added to a mixture of 2.74g (10.8mmol) of 4-[4-(trifluoromethyl) phenoxy] aniline and 2.5ml (18.3mmol) of triethylamine in 40ml of diethyl ether. The resulting mixture is stirred at room temperature for 4 hours and left to stand at room temperature overnight. The resulting suspension is filtered, the filtrate is washed with a saturated sodium chloride solution, then dried and concentrated to give a brown solid which is chromatographed (ethyl acetate/heptane) to give 1.2g (63%yield) of an orange solid (M+1 =410).

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer CropScience S.A.; EP1275301; (2003); A1;,
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Electric Literature of 583-19-7, 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. 583-19-7, name is 1-Bromo-2-ethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) 4-(3-bromo-4-ethoxyphenyl)-4-oxobutanoic acid To a suspension of bromo-2-ethoxybenzene (12.0 g) and succinic anhydride (6.9 g) in dichloromethane (40 mL) was gradually added aluminum chloride (19.0 g) under ice-cooling, and the mixture was heated with stirring at 50C for 0.5 hr. The reaction mixture was cooled, and poured into concentrated hydrochloric acid (100 mL)-ice. The mixture was stirred for 1 hr, and extracted with ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 4-(3-bromo-4-ethoxyphenyl)-4-oxobutanoic acid (6.5 g) as crude crystals. 1H-NMR (CDCl3)delta: 1.51(3H, t, J=7.2Hz), 2.74(2H, t, J=6.6Hz), 3.34(2H, t, J=6.6Hz), 4.19(2H, q, J=7.2 Hz), 6.92(1H, d, J=8.7Hz), 7.92(1H, dd, J=8.7Hz, 2.4Hz), 8.19(1H, d, J=2.4Hz)

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1845081; (2007); A1;,
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Application of 5414-19-7, 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. 5414-19-7 name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Step 1: Ethyl 4-(4-bromophenyl)tetrahydro-2H-pyran-4-carboxylate 6.0 g (24.7 mmol) of ethyl 4-bromophenylacetate were dissolved in 120 ml of abs. DMF under argon, 1.48 g (37.0 mmol, 60% strength) of sodium hydride were added, while cooling in an ice bath, and the mixture was stirred for 30 min. 5.72 g (24.7 mmol) of bis(2-bromoethyl)ether were then added, while constantly cooling in an ice bath, and the mixture was stirred at approx. 0 C. for 1 h. After renewed addition of 1.48 g of 60% strength sodium hydride, the mixture was stirred again for 1 h, while cooling in an ice bath. Saturated aqueous ammonium chloride was then added and the mixture was extracted with ethyl acetate. The organic phase was washed with water and with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The residue was purified by column chromatography over silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 2.62 g (33% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, delta/ppm): 7.47 (d, 2H), 7.25 (d, 2H), 4.14 (q, 2H), 3.93 (dt, 2H), 3.56 (td, 2H), 2.59 (dd, 2H), 1.93 (m, 2H), 1.19 (t, 3H). MS (DCI, NH3): m/z=329 [M+NH4]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-(2-bromoethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
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Application of 59557-91-4, 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. 59557-91-4 name is 4-Bromo-2-methoxyaniline, 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.

4-Bromo-2-methoxyaniline (2.00 g, 9.90 mmol) were dissolved in water (10 mL) and concentrated hydrochloric acid (3 mL). The mixture was cooled in ice-salt bath, then a solution of sodium nitrite (0.69 g, 9.8 mmol) in water (4 mL) was added dropwise slowly while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 5 min. The mixture described above was added to a mixture of sodium acetate trihydrate (8.75 g, 64.3 mmol), ethyl isocyanoacetate (1.0 mL, 9.15 mmol) and MeOH/H2O (22 mL, 10/1) while maintaining the temperature at 0-5 C. After the addition, the mixture was stirred at 0C for 30 min, then warmed to rt for further 3 h. After the reaction was completed, the mixture was concentrated to remove most of the solvent. The residue was filtered, and the filter cake was washed with cool water. The filter cake was dried in vacuo to give a reddish brown solid (2.65 g, 82.1%). MS (ESI, pos.ion) m/z: 327.1 (M+2)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
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Synthetic Route of 60789-54-0, A common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)benzene, molecular formula is C11H15BrO, 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 115 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.1 g) as starting compound, potassium carbonate (1.5 g) and 4-benzyloxybutyl bromide (1.0 g) were reacted and treated in the same manner as in Example 52 to give 0.32 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-benzyloxybutyl)piperidin-4-yl)methyl)benzamide. 1H-NMR (CDCl3,ppm)delta:1.40-1.81(9H,m), 2.82(2H,t), 2.98(2H,t), 3.20(2H,t), 3.44(4H,m), 3.82(3H,s), 4.45(3H,s), 5.93(2H,s), 6.48(1H,s), 7.33-7.45(5H,m), 7.66(1H,s), 8.00(1H,t)

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; YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.; EP873990; (1998); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, 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 35822-58-3, Safety of 2-Bromobenzaldehyde diethyl acetal

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.

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-Bromobenzaldehyde diethyl acetal, other downstream synthetic routes, hurry up and to see.

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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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. 101-55-3, name is 1-Bromo-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H9BrO

To 260 ml toluene, 108 g para cresol and 80 g 50% caustic lye are added and the water is azeotropically distilled out. To the mass 50 ml DMF, 249 g 4-bromodiphenyl ether and 5 g CuBr are added. The mass is maintained at 150-165C for 6 hrs, cooled to 100C and filtered. The filtrate on fractional distillation gave 235 g (85% yield) of 1-(4-methytphenoxy),4-phenoxybenzene, b.p. 200-201 C/4 mm Hg pr., m.p. -53-54C

The synthetic route of 101-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gharda Chemicals Limited; EP1454891; (2004); A1;,
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