Month: June 2021

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. 89-91-8, name is Methyl 2,2-dimethoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 89-91-8

A diethyl ether solution of ethylmagnesium bromide (concentration=2 1.85 mass %, 277 g) was added to a reaction flask and was cooled to around 0 C. by stirring on an ice-cooling bath. A Grignard reaction was carried out by the dropwise addition to this solution over one hour of methyl dimethoxyacetate (25 g). This was followed by return to room temperature and reaction for 12 hours. The reaction solution was ice-cooled; 200 g of a saturated aqueous ammonium chloride solution was added dropwise; and the pH was subsequently adjusted to around neutrality by the dropwise addition of 10 mE of a 36% hydrochloric acid solution. The solution was then transferred to a separatory funnel; the organics were extracted with 50 g of hexane and separated; and drying was carried out over an appropriate amount of magnesium sulfate. This hexane suspension was filtered followed by removal of the solvent on an oil bath at around 65 C. Distillation was performed under reduced pressure on an oil bath at around 100 C. to obtain 22.4 g of a transparent and colorless 3-dimethoxym- ethyl-3-pentanol (GC purity=96.3%). 10 g of pure water and 1 g of 36% hydrochloric acid were added under ice cooling to 7 g of the 3-dimethoxymethyl-3-pentanol and stirring was carried out overnight. After this, 9.5 g of a 33% aqueous ethylamine solution was added dropwise under ice cooling and a reaction was run for 10 hours. The pH of the reaction solution at this time was 10 to 11. When stirring was stopped, separation occurred into an aqueous layer and a small amount of an organic layer, and the organic layer was determined to be alcohol compound No. 140 according to the NMR results. 2.7 g of the target was obtained for a yield of 33%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 89-91-8.

Reference:
Patent; ADEKA CORPORATION; SAKURAI, Atsushi; HATASE, Masako; YOSHINO, Tomoharu; ENZU, Masaki; (40 pag.)US2017/129912; (2017); A1;,
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Electric Literature of 15963-40-3, 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. 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry three-neck flask was charged with methyl 3-methylenecyclobutanecarboxylate (6 g, 47.6 mmol) and dry THF (20 ml) and cooled to -10 C. BH3.THF (12.26 g, 143 mmol) was then added via a syringe dropwise. The resulting mixture was stirred for 4h at rt and was cooled to -20 C – 10C. Methanol was then added and the mixture was stirred for 15min. Sodium hydroxide (3M; 30 ml) and H2O2 (7.29 ml_, 238 mmol) were added in sequence. The mixture was stirred for 2h and a saturated sodium sulfite solution (100 ml) was added. The reaction mixture was diluted with water, then extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and the residue was purified by flash chromatography eluting with (petroleum ether/EtOAc = 3/1 ) to afford methyl 3- (hydroxymethyl)cyclobutanecarboxylate (250 mg, 1 .387 mmol, 2.92 % yield) as a yellow oil.

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 3-methylenecyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

34846-90-7, name is Methyl 3-methoxyacrylate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C5H8O3

To a solution of 1,1,2,2-tetrafluoroethyldimethylamine (96percent, 46 g, 305 mmol) in acetonitrile (100 ml) was added dropwise, at 25° C. under Argon, BF3-etherate (38.9 g, 274 mmol). Subsequently, under reflux conditions (approx. 70° C.), a solution of methyl 3-methoxyacrylate (95percent, 33.5 g, 274 mmol) in acetonitrile (75 ml) was added dropwise to the reaction mixture within 1 h. After stirring under reflux conditions for 21 h, the reaction mixture was cooled to 25° C. The resulting reaction mixture was added dropwise to a solution of methylhydrazine (21 g, 457 mmol) in acetonitrile (48 ml) at 0 to 15° C. within 1.5 h. After stirring at 25° C. for 0.5 h, water (100 ml) was added. The reaction mixture was extracted once with 150 ml and once with 90 ml of methylene chloride. The combined organic phases were washed with water (1.x.200 ml). The resulting organic phase (530 g) contained, according to GC area percent analysis, methyl 3-difluoromethyl-1-methylpyrazole-4-carboxylate and methyl 5-difluoromethyl-1-methylpyrazole-4-carboxylate in a ratio of 6.8:1. According to quantitative HPLC analysis, the organic phase comprised 6.7percent by weight of methyl 3-difluoromethyl-1-methylpyrazole-4-carboxylate. This corresponds to a yield of 68percent (based on methyl 3-methoxyacrylate).

The synthetic route of 34846-90-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; US2010/184994; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 27492-84-8, These common heterocyclic compound, 27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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.

2.1) Diphenyl ether (500 mL, 3.15 mol) was added to a 1 L three-necked flask.After preheating the diphenyl ether in the three-neck flask to 220°C, add step 1.4).Compound II (45.25 g, 0.25 mol) and ethoxylated methyl malonate IIEthyl ester (58.32g, 0.27mol), reaction 1h, to obtain a mixture D;2.2) stirring the mixture D obtained in step 2.1) until it is cooled to 50 ° C to obtain a mixture E;2.3) The mixture E obtained in step 2.2) is filtered, the solid obtained after filtration is washed with methyl tert-butyl ether and dried to obtain compound III (yield 94.59percent)

Statistics shows that Methyl 4-amino-2-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 27492-84-8.

Reference:
Patent; Chongqing University; Dong Lichun; Hu Geng; Li Qi; Liu Dianqing; Wang Haoyuan; (19 pag.)CN107629001; (2018); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16017-69-9, name is Ethyl 4-amino-2-chlorobenzoate, 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 16017-69-9, name: Ethyl 4-amino-2-chlorobenzoate

The indicated chloro-aniline (1.02 g, 5.125 mmol) in methanol (13.0 mL) was treated with iodine monochloride (1.0 M in dichloromethane, 5.125 ml, 5.125 mmol) and the solution stirred for 1 hour at room temperature. The reaction mixture was poured into water, followed by aqueous/ethyl acetate work- up, and silica gel chromatography (ethyl acetate : hexanes (2:8) 3.0 % TEA) to give the titled compound.

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; MERCK & CO., INC.; WO2007/81335; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 39503-58-7, 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. 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Description 44Methyl 4-methyl-2-(methyloxy)-5-(trifluoromethyl)benzoate (D44)To a mixture of methyl 5-bromo-4-methyl-2-(methyloxy)benzoate (may be prepared as described in Description 43; 2.5 g, 9.65 mmol) in N,N-dimethylformamide (40 ml) was added copper (I) iodide (4.04 g, 21.23 mmol) and potassium trifluoroacetate (2.94 g, 19.30 mmol). Toluene (10 ml) was added and the mixture heated in Dean Stark apparatus at 170C for 45 minutes. The toluene was removed via the Dean Stark trap and the resulting mixture was heated for 18 hours at 170C. The mixture was diluted with water (10 ml) and ethyl acetate (20 ml) and the solid was removed using Celite. The filtrate was taken and the organic layer separated, dried (MgS04) and the solvent removed in vacuo. The residue was purified by column chromatography (Si02, 50% Cyclohexane/diethyl ether) to yield the title compound as a white solid. 1.76 g.MS (electrospray): m/z [M+H]+ 249

The synthetic route of Methyl 5-bromo-2-methoxy-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; ANDREOTTI, Daniele; DAI, Xuedong; EATHERTON, Andrew John; JANDU, Karamjit Singh; LIU, Qian; PHILPS, Oliver James; WO2012/28629; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 75567-84-9, The chemical industry reduces the impact on the environment during synthesis 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, I believe this compound will play a more active role in future production and life.

(Example 65) 3-(4′-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)propanoic acid (Exemplification Compound No.: 1-67) According to a method similar to Example (31) and Example (17-4), from methyl 3-(4-bromophenyl)propionate (131 mg, 0.51 mmol) and tert-butyl 2-hydroxy-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (250 mg, 0.51 mmol) obtained in Example (22-4), the title compound was obtained as a colorless powder (26 mg, yield: 10%). 1H-NMR (400MHz, DMSO-d6): delta 12.09 (1H, br), 11.40 (1H, br), 7.79 (1H, d, J = 7.8 Hz), 7.58 (2H; d, J = 8.6 Hz), 7.50 (2H, d, J = 8.6 Hz), 7.28-7.24 (3H, m), 7.03 (2H, d, J = 8.6 Hz), 5.35 (2H, s), 2.83 (2H, t, J = 7.8 Hz), 2.55 (2H, t, J= 7.8 Hz), 1.56 (9H, s). MS (FAB+) (m/z): 516 (M+.).

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 3-(4-bromophenyl)propanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP1806332; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 1117-71-1, A common heterocyclic compound, 1117-71-1, name is Methyl 4-bromobut-2-enoate, molecular formula is C5H7BrO2, 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.

To a stirred homogeneous solution of (E)-methyl 4-bromobut-2-enoate (53.7 g, 300 mmol) in THF (100 mL) at 0 C (bath temperature) under a nitrogen atmosphere, was added a solution of lithium hydroxide monohydrate (16.4 g, 390 mmol) in water (80 mL) dropwise (over 35 min). After addition the mixture was stirred at 0 “C for 3 h. Cold water (300 mL) and petroleum ether (400 mL) were added and the mixture was stirred at 0 C for 10 min. The organic layer was separated and discarded. Ethyl acetate/petroleum ether (1:10, 300 mL) was then added and-the mixture was again stirred at 0 C for 10 min before the organic layer was separated and discarded. The aqueous solution was acidified with cone, sulfuric acid at 0 C to pH <; 1. The product was extracted into dichloromediane (400 mL; 200 mL) and the combined organic extracts were dried (MgSO4) and evaporated under reduced pressure at 35 C (bath temperature) to give a yellow oil. The oil was stirred with petroleum ether (2x500 mL) at 50 C (bath temperature). The combined petroleum ether extracts were concentrated under reduced pressure at 20-25 C (bath) to induce precipitation of the product The suspension was then stood at 5 UC overnight before the solid was collected by filtration, washed with cold petroleum ether and dried to give (E)-4-bromobut-2-enoic acid (9) (19.9g, 40%). The synthetic route of 1117-71-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AUCKLAND UNISERVICES LIMITED; SMAILL, Jeffrey, Bruce; PATTERSON, Adam Vorn; DENNY, William, Alexander; WILSON, William Robert; LU, Guo-Liang; ANDERSON, Robert, Forbes; LEE, Ho Huat; ASHOORZADEN, Amir; WO2010/104406; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 878207-28-4, name is Methyl 2-bromo-4,5-difluorobenzoate, 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 878207-28-4, Application In Synthesis of Methyl 2-bromo-4,5-difluorobenzoate

A solution of the intermediate methyl 2-bromo-4,5-difluorobenzoate (4.4g, 17.53mmol) and benzylamine (2.066g, 2.108mL, 19.28mmol) in N,N-dimethylsulfoxide was treated with dibasic potassium phosphate (12.21g, 70.1 mmol) and heated to 75C for 18 hours in an open tube. The reaction mixture was then diluted with of ethyl acetate (20OmL), washed with of water (4x15OmL) and saturated brine before drying (sodium sulfate) and evaporation to yield the title compound (5.3g). 1H NMR (CDCI3, 400 MHz):delta 3.86 (2H, s), 4.40, (2H, d), 4.69 (1 H, br s), 6.91 (1 H, d), 7.35 (5H, m), 7.63 (1 H, d)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-4,5-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; N.V. ORGANON; WO2009/138438; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 29263-94-3, A common heterocyclic compound, 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, molecular formula is C8H13BrO4, 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.

A mixture of diethyl 2-bromo-2-methylmalonate (1 equiv.), malononitrile (1 equiv.) and potassium t-butoxide (1 equiv.) in THF was heated to reflux for 15 h. The mixture was diluted with ethyl acetate and saturated aqueous ammonium chloride solution and the phases were separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to give an oil. The oil was purified by silica gel chromatography (10-15% ethyl acetate in hexane gradient) to give diethyl 2-(dicyanomethyl)-2-methylmalonate (5.76 g, 32 % yield) as a colorless oil.1H NMR (500 MHz, CDC13) oe ppm 4.53 (s, 1 H), 4.27 – 4.39 (m, 4 H), 1.81 (s, 3 H), 1.33 (t, 6H).

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NAKAI, Takashi; MOORE, Joel; PERL, Nicholas Robert; IYENGAR, Rajesh R.; MERMERIAN, Ara; IM, G-Yoon Jamie; LEE, Thomas Wai-Ho; HUDSON, Colleen; RENNIE, Glen Robert; JIA, James; RENHOWE, Paul Allen; BARDEN, Timothy Claude; YU, Xiang Y; SHEPPECK, James Edward; IYER, Karthik; JUNG, Joon; WO2014/144100; (2014); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics