Author: Jessica.F

Synthetic Route of 27798-60-3, The chemical industry reduces the impact on the environment during synthesis 27798-60-3, name is Methyl 2-Methoxyphenylacetate, I believe this compound will play a more active role in future production and life.

A 5 OOmL round-bottom flask is charged with methyl 2-(2-methoxyphenyl)acetate (8.496 g, 47 mmol, leq) and THF (200mL). The homogeneous mixture is cooled to 0 C in an ice bath. Lithium diisopropyl amide (23.5mL of a 2.OM solution in heptane/THF) is added,maintaining a temperature less than 3C. The reaction is stirred 45 minutes at this reduced temperature. Benzyl bromide (5.6mL, 47mmol, leq) is added dropwise. The reaction is allowed to gradually warm to room temperature and is stirred for 18 hours. The reaction is quenched with iN HC1 and extracted 3 times with equal portions of EtOAc. The combined extracts are washed with H20 and brine, dried over Na2SO4,filtered, and concentrated. The residue is purified over silica to afford 4.433g (35%) of the desired compound. ESI+ MS 293 (M+Na).

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, Methyl 2-Methoxyphenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AERPIO THERAPEUTICS INC.; PETERS, Kevin; SHALWITZ, Robert; JANUSZ, John; SMITH, Alexander; WO2014/145068; (2014); 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. 35450-36-3, name is Methyl 2-bromo-5-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H9BrO3

Under an argon atmosphere, 2.300 g (approx. 10.298 mmol) of the compound from example 51A was dissolved in 20 ml toluene and 2.103 g (8.585 mmol) of methyl-2-bromo-5-methoxybenzoate, 2.551 g (12.014 mmol) potassium phosphate, 0.346 g (1.159 mmol) of (2-biphenyl)di-tert.- butylphosphine and 0.173 g (0.772 mmol) of palladium(II) acetate were added. The mixture was boiled under reflux overnight. After cooling, it was extracted with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated in a rotary evaporator at reduced pressure. The residue was purified by preparative HPLC (eluent: acetonitrile/water, gradient 10:90 ? 90:10). We obtained 135 mg (4% of theor.).LC-MS (method 4): R, = 1.28 min; MS (EIpos): m/z = 368 [M+H]+.1H-NMR (400 MHz, DMSO-D6): delta [ppm] = 2.20 (s, 3H), 3.70 (s, 3H), 3.80 (s, 3H), 3.84 (s, 3H), 6.07 (s, IH), 7.04 (dt, IH), 7.11 (dd, IH), 7.16-7.24 (m, 2H), 7.30 (d, IH), 7.34 (dd, IH), 7.41-7.46 (m, IH), 9.14 (sbr, IH).

The synthetic route of 35450-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; KAST, Raimund; GRIEBENOW, Nils; MEIER, Heinrich; KOLKHOF, Peter; ALBRECHT-KUePPER, Barbara; NITSCHE, Adam; STASCH, Johannes-Peter; SCHNEIDER, Dirk; TEUSCH, Nicole; RUDOLPH, Joachim; WHELAN, James; BULLOCK, William; PLEASIC-WILLIAMS, Susan; WO2010/20363; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, belongs to esters-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 33689-29-1, Recommanded Product: 33689-29-1

To a solution of methyl l-hydroxycyclopropanecarboxylate (1.0 g, 8.62 mmol) and 3,4-dihydropyrane (0.86 mL, 9.42 mmol) in dichloromethane (20 mL) was added pyridinium-/ -tolucnc sulfonic acid (216 mg, 0.86 mmol) at RT. The mixture was stirred overnight at RT. The solvent was removed under vacuum and the residue was purified by flash column chromatography to yield 990 mg of the desired product. NMR (400 MHz, CDCb) d 1.30-1.32 (m, 2H), 1.54-1.58 (m, 6H), 1.82-1.85 (m, 2H), 3.47-3.53 (m, 1H), 3.74 (s, 3H), 3.83-3.89 (s, 1H), 4.89-4.91 (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; ICHNOS SCIENCES S.A.; CHAUDHARI, Sachin, Sundarlal; GHARAT, Laxmikant, Atmaram; IYER, Pravin; DHONE, Sachin, Vasantrao; ADIK, Bharat, Gangadhar; WADEKAR, Prashant, Dilip; GOWDA, Nagaraj; BAJPAI, Malini; (233 pag.)WO2020/70331; (2020); A1;,
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Reference of 541-16-2, These common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, 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.

General procedure: alpha,beta-Unsaturated aldehyde (3.0 mmol) and malonate (3.0 mmol) were added into asolution of TiCl4 (6.0 mmol) in CCl4 (2.0 mL) and THF (10 mL) at 0 C, Then, pyridine (0.96 mL, 12.0 mmol) in THF (2 mL) was added dropwisely over 1 h. The resulting mixture was stirred at room temperature overnight. After quenched with water, the mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography with hexane/ethyl acetate = 20/1 to afford the product.

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Xu; Lu, Junzhu; Duan, Wei-Liang; Synthesis; vol. 48; 23; (2016); p. 4155 – 4160;,
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Electric Literature of 5445-17-0, A common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, molecular formula is C4H7BrO2, 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.

The 2.50g (9.05mmol) of tert-butyl 2 – [(benzylamino) methyl] azetidine-1-carboxylate [racemate] was dissolved in dichloromethane (150ml), the 5.55ml (4.03g, 39.8mmol) of triethylamine and 3.04ml (4.53g, 27.1mmol) of methyl 2-bromo-propionate [racemate] was added and the mixture was stirred overnight at room temperature.Then 5.55ml (4.03g, 39.8mmol) of triethylamine and 3.04ml (4.53g, 27.1mmol) of methyl 2-bromopropionate [racemate] was added, and the mixture was at 40 stirred overnight.At 40 then added 5.55ml (4.03g, 39.8mmol) of triethylamine and 3.04ml (4.53g, 27.1mmol) of methyl 2-bromopropionate [racemate], and the mixture was stirred overnight.After cooling to room temperature, the mixture was diluted with dichloromethane and washed with water, and the phases were separated.The aqueous phase was extracted twice with dichloromethane and the combined organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and then the solvent was removed under reduced pressure.The crude product obtained was purified as follows: silica gel chromatography (dichloromethane, then dichloromethane / methanol = 100: 1).Yield: 3.22g (94%, based on the theoretical value).

The synthetic route of 5445-17-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma AG; Aleihailigen, S.; Buhemilei, A.; Engeer, K.; Gedesi, C.; Gelike, K.M.; Gelishi, M.; Haitemaier, S.; Xilishi, A.; Jinceer, T.; Linao, P.; Lideer, B.; Leilixi, S.; Shimite, M.V.; Shitelasibuge, J.; Teshitegen, A.; (253 pag.)CN105431428; (2016); A;,
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These common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, 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. name: Ethyl 2-butynoate

General procedure: To a solution of 2-aminoaryl carbonyl 1 (0.5 mmol), MCM-41-PPh3-AuCl (128 mg, 0.05 mmol), AgOTf (12.9 mg, 0.05 mmol) in DMF (5 mL) was added internal alkyne 2 (0.75 mmol) under Ar. The reaction mixture was stirred at 100C for 4 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (20 mL) and filtered. The gold catalyst was washed with NH3·H2O (2 × 5 mL), distilled water (5 mL), and acetone (2 × 5 mL) and reused in the next run. The filtrate was washed with water (2 × 10 mL) and brine (2 × 10 mL), and the organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 15/1) to afford the desired product 3.

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

Reference:
Article; Hu, Wenli; Yang, Weisen; Yan, Tao; Cai, Mingzhong; Synthetic Communications; vol. 49; 6; (2019); p. 799 – 813;,
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Application of 14062-24-9, 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 14062-24-9 as follows.

Ethyl trifluoroacetate (3.57 g, 25.2 mmol) and sodium (580 mg, 25.2 mmol) were added to a solution of ethyl 2-(4-chlorophenyl)acetate (5.0 g, 25.2 mmol) in ether (8 mL), followed by heating to reflux for 24 hours. After the reaction was completed, 2N hydrochloric acid (50 mL) was added thereto, and the resultant product was extracted with ether (20 mL*3). The mixed organic layer was washed with water (20 mL*3), and dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1), whereby ethyl 2-(4-chlorophenyl)-4,4,4-trifluoro-3-oxobutanoate (2.42 g, yield: 34%) was obtained as a yellow solid.

According to the analysis of related databases, 14062-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); A1;,
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These common heterocyclic compound, 2065-23-8, name is Methyl 2-phenoxyacetate, 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. SDS of cas: 2065-23-8

To the methyl phenoxyacetate obtained by distillation,0.09 g of 99% pure lead acetate and 1.29 g of 99% pure 2,3,4-trichlorothiophene were added.118.34 g of 99% pure thionyl chloride was added dropwise at 20 C to react.After the addition, the reaction was kept at this temperature for 0.5 h.The fraction was distilled at a pressure of 1 kPa and collected at 110 to 120 C to obtain 200.87 g of methyl 4-chlorophenoxyacetate, and the content was 98.84%.

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

Reference:
Patent; Shandong Runbo Biological Technology Co., Ltd.; Sun Guoqing; Hou Yongsheng; Chi Zhilong; Zhang Liguo; Hu Yishan; (13 pag.)CN108947839; (2018); A;,
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Electric Literature of 104670-74-8, The chemical industry reduces the impact on the environment during synthesis 104670-74-8, name is Methyl 2-amino-3-bromobenzoate, I believe this compound will play a more active role in future production and life.

Example 83: Synthesis of 2-amino-3-[2-(3- hydroxyphenyl)ethynyl]benzoic acid 2-amino-3-[2-(3-hydroxyphenyl)ethynyl]benzoic acid: To a sealed tube was loaded a mixture of 2-amino-3-bromo-benzoic acid methyl ester (50 mg, 0.22 mmol), Pd(PPh3)2Cl2 (15.4 mg, 0.022 mmol) and Cul (4.2 mg, 0.022 mmol) in triethyl amine (1 mL). The mixture was degassed with N2 for 10 minutes, 3- ethynyl-phenol (103 mg, 0.87 mmol) was added and the mixture degassed with N2 for 5 minutes. The reaction mixture was heated at 90 C for 5 hours. After cooling to ambient temperature, the crude mixture was filtered through celite and washed with dichloromethane. The filtrate was concentrated and purified by preparative thin layer chromatography eluting with ethyl acetate/hexane (30%) to give a solid intermediate. To the solid intermediate in tetrahydrofuran/methanol (1 mL/0.2 mL) was added sodium hydroxide solution (2 N in water, 0.2 mL, 0.4 mmol) and the solution was stirred at room temperature for 18 hours. 1 N hydrochloric acid aqueous solution was added dropwise until pH = 1 and the reaction mixture was purified through preparative HPLC to give 11 mg (14% for 2 steps) of the pure product as a white solid. LCMS (ESI) mlz 254.1 (M+l)+.

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, Methyl 2-amino-3-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE WISAR INSTITUTE OF ANATOMY AND BIOLOGY; MESSICK, Troy, E.; SMITH, Garry, R.; REITZ, Allen, B.; LIEBERMAN, Paul, M.; WO2015/73864; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35065-86-2, name is 3-Bromophenyl acetate, belongs to esters-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 35065-86-2, Safety of 3-Bromophenyl acetate

In a 250 mL round bottom flask (8) (5.49 g, 26 mmol) and anhydrous AlCl3 (6.92 g, 51 mmol) was mixed thoroughly on oil bath at 160 C for 2 h. Reaction mixture was poured into ice water and concentrated hydrochloric acid solution was added to break complex formed during reaction. The mixture was taken in AcOEt (50 mL * 3). The organic layer was combined and washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 30:1) gave (9) (3.85 g, 70 %) as white solid. Mp: 36-38 C, MS (EI) [M]+: m/z = 213, 1H NMR (400 MHz, CDCl3) delta ppm: 7.60 (d, J = 8.0 Hz, 1H), 7.20 (s, 1H), 7.07 (d, J = 8.0 Hz, 1H), 2.63 (s, 3H).

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

Reference:
Article; Wang, Chen; Gao, Hongping; Dong, Jinyun; Zhang, Yanmin; Su, Ping; Shi, Yaling; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 22; 1; (2014); p. 277 – 284;,
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