Month: April 2021

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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Related Products of 36865-41-5, 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. 36865-41-5 name is 1-Bromo-3-methoxypropane, 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.

A mixture of 5-bromo-2-chloro-phenol (22.0 g, 106 mmol), l-bromo-3-methoxy-propane (19.5 g, 127 mmol) and K2C03 (30 g, 212 mmol) in DMF (50 mL) was heated at 50 C for 3 hrs. Then the mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried over anhydrous Na2S04 and concentrated under reduced pressure to give crude 4-bromo-l-chloro-2-(3-methoxypropoxy)benzene (30.0 g), which was used directly in the next step without further purification

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JIANG, Min; YANG, Song; (109 pag.)WO2016/128335; (2016); A1;,
Ether – Wikipedia,
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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;,
Ether – Wikipedia,
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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;,
Ether – Wikipedia,
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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. 36865-41-5, name is 1-Bromo-3-methoxypropane, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H9BrO

A solution of compound of Formula-Ill (lOOg) in toluene (600 ml) and Dimethylsulfoxide (60 ml) was added to potassium carbonate (185g) and l-Bromo-3-methoxypropane (130g) at 25-30C. The resulting reaction mixture was stirred at 85- 90C for 16h. After cooling, the solid was filtered and washed with water. The toluene layer of compound of Formula-IV was cooled to 0-5C and sodium borohydride (9gm) was added. To this reaction mixture methanol (50 ml) was added drop wise at 0-5C over a period of lh and stirred the reaction mixture at the same temperature for 2h. The reaction was quenched with dilute hydrochloric acid and stirred for 30 minutes. pH of the reaction mixture was adjusted to 7.0-7.5 with aq. Sodium hydroxide solution. Organic layer was separated and aqueous layer was extracted with toluene. Combined organic layers were dried and evaporated under reduced pressure to give compound of Formula- IV as residue. The residue was dissolved in dichloromethane and added to a solution of thionyl chloride in dichloromethane at 0-5C over a period of lh and stirred the reaction mixture at the same temperature for 2h. Dichloromethane was distilled under reduced pressure at 30-35C till no more distillate was collect. The compound was re-crystallized in hexanes to give tile compound as white solid. Yield: 125g; GC purity: 99%.

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; MYLAN LABORATORIES LIMITED; RAMA, Shankar; VADALI, Lakshmana Rao; MANUKONDA, Seshadri rao; POTLA, Venkata Srinivas Rao; VADLAMUDI, Mohana Vamsi Krishna; DASARI, Srinivasa Rao; WO2013/171767; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 4003-89-8, 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 4003-89-8 as follows.

Example 16: Benzoic acid 2-[3-(7-methoxy-1 ,2,3,4-tetrahydro-naphthalen-2-yl)-thioureido]-ethyl ester (compound 16); A solution of 7-methoxy-1 ,2,3,4-tetrahydro-naphthalen-2-ylamine (0.34 g) in toluene (10 ml) was treated with benzoic acid 2-isothiocyanato-ethyl ester (0.39 g, cf. Collect. Czech. Chem Commun. 1986, 51, 112-117), refluxed for 1 h and stirred at room tem- perautre overnight. Purification by Chromatography on silica gel yielded the product (0.32 g), m.p. 103-106 0C.

According to the analysis of related databases, 4003-89-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF SE; WO2008/145615; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 5414-19-7, A common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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.

Step 1 Preparation of 4-(4-(trifluoromethyl) phenyl)-tetrahydro-2H-pyran-4-carbonitrile To a stirred solution of 2-(4-(trifluoromethyl)phenyl)acetonitrile (2.0 g, 10.8 mmol) in DMF (10 mL) was slowly added a suspension of NaH (60%, 0.95 g, 23.7 mmol) in DMF (10 mL) at 0 C. under N2 atmosphere over 10 min, the reaction was allowed to warm to room temperature and stirred for 0.5 h. Then the reaction was cooled to 0 C. and 2,2′-dibromodiethyl ether (1.5 mL, 11.8 mmol) in DMF (20 mL) was added dropwise over 60 min. The reaction was allowed to warm to room temperature and stirred for 1 h. The mixture was quenched with water (30 mL) and extracted with EtOAc (30 mL*3). The combined organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified with column chromatography on silica gel (petroleum ether_EtOAc=100:1) to afford 4-(4-(trifluoromethyl)phenyl)-tetrahydro-2H-pyran-4-carbonitrile (2.30 g, 83%) as red oil. GC-MS: [M]+ 255; tR=10.39 min.

The synthetic route of 5414-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; KARRA, Srinivasa R.; (153 pag.)US2016/168090; (2016); 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., Recommanded Product: Perfluoro(2-methyl-3-oxahexanoyl) fluoride

The same operation as in Example 1-1 was carried out except that the starting materials were changed as shown in Table 1.The GC purity of the recovered crude liquid was 97%.In addition, measurement1the H-NMR and19F.-NMR spectra confirmed the title compound as a main component (fluorine content = 58.5% by mass)

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; Asahi Glass Co Ltd;; Qing, Shanyuanzhi; Ye, Cunshunping; (28 pag.)CN105492418; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem