Category: esters-buliding-blocks

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;,
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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;,
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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;,
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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;,
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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;,
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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,
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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;,
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Reference of 56741-34-5, 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. 56741-34-5 name is Methyl 5-amino-2-fluorobenzoate, 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 A: Methyl 5-{[(2,6-difluorophenyl)carbonyl]amino}-2-fluorobenzoate; To a solution of methyl 5-amino-2-fluorobenzoate (2.5 g, 14.8 mmol) (prepared according to literature precedence) in DCM (100 mL) at 0 0C, 2,6-difluorobenzoyl chloride (1.85 mL, 14.8 mmol) was added and the solution was allowed to stir for 30 min. The reaction mixture was quenched with H2O (50 mL). The organic layer was then washed with 1M NaOH (50 mL), dried over MgSO4, filtered and evaporated onto silica gel. The title compound of Step A was purified by chromatography, (25-100% EtOAc in hexanes). The title compound of Step A was obtained as a white solid in 69% yield (3.17 g). MS (ESI): 309.99 [M+H]+.

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/76140; (2009); A1;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 34529-06-1, name is Dimethyl 3-aminophthalate, 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 34529-06-1, Product Details of 34529-06-1

Methyl-3-cyano-2-(methoxycarbonyl)benzoate To a stirred suspension of methyl-3-amino-2-(methoxycarbonyl)benzoate (17.0 g, 81 mmol) in a mixture of concentrated HCl (44 ml) and water (440 ml) at 4 C. was added a solution of NaNO2 (6.73 g, 97 mmol) in water (25 ml) dropwise at 4-5 C. Stirring was continued for 30 min at 4 C. The mixture was then carefully neutralized with sat. sodium carbonate to pH 6. A stirred solution of CuCN (9.46 g, 105 mmol) and KCN (6.38 g, 105 mmol) in water (150 ml) was warmed to 60 C. The cold neutralized diazonium solution was then added in small portions at a time with vigorous stirring. The mixture was stirred at 60 C. for 1 hour and then cooled to room temperature. The mixture was extracted with dichloromethane (4*150 ml) and the combined dichloromethane extracts were washed with water (2*100 ml), brine (100 ml) and dried. The solvent was removed in vacuo and the product was purified by chromatography (dichloromethane) to afford 12.36 g (65%) of the product as a light yellow solid: 1H NMR (CDCl3) delta8.19 (d, J=7.9 Hz, 1H), 7.89 (d, J=7.4 Hz, 1H), 7.64 (t, J=8.0 Hz, 1H), 4.03 (s, 3H), 3.94 (s, 3H).

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; Robarge, Michael J.; Chen, Roger Shen-Chu; Muller, George W.; Man, Hon-Wah; US2003/96841; (2003); A1;,
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Ester – an overview | ScienceDirect Topics

Synthetic Route of 51122-91-9, 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. 51122-91-9, name is Dimethyl Isopropylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1; 382g (406ml) of DMF were initially charged in a Schmizzo and 137g (141 ml) of 1.0 eq. NaOMe (30% solution in methanol) were added. This mixture was then heated to 600C (+ 3C) and 131g (0.753mol) of dimethyl isopropylmalonate were metered in within one hour. Subsequently, a methanol/DMF mixture (201 g) was distilled off under pressure (300 mbar to 60 mbar) and a temperature of 600C. Thereafter, at 800C (+ 30C), 86 g (79 ml, 0.779 mol, 1.03 eq.) of 1 ,3-dichloropropene were metered in within one hour and the reaction mixture was then heated at 800C (+ 3C) for two hours.The reaction mixture was heated to 1400C and a 25% solution of LiCI (0.6 eq.) in methanol (19 g of LiCI in 58 g of methanol) was metered in within two hours, and the reaction mixture was heated at 140-1420C for a further 6 hours, in the course of which a portion of the methanol was distilled off and approx. 1.5 mol of gas (mainly CH3CI and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters.On completion of reaction, the solvent (DMF) and the excess methanol were distilled off substantially fully under reduced pressure. The remainder was admixed with 200 g of water, 89 g of 34% HCI and 200 g of MTBE, and the phases were separated. The organic phase was washed 1x with 50 g of water and the solvent was removed under reduced pressure. Approx. 140 g of product were obtained, of which approx. 125 g were ester and 13 g the corresponding acid.To prepare the corresponding acid, the above product was processed further. 140 g of crude product were suspended in 15O g of water and 70 g of 50% NaOH (1.15 eq.) were added. The reaction mixture was initially charged in an autoclave and heated at max. 3 bar and a temperature of 100-1100C for two hours. On completion of reaction, the methanol formed was distilled off via the top. Thereafter, the mixture EPO was adjusted to pH 1.5 with H2SO4 (76%) and extracted 2x with 100 g of IPAT each time, and the solvent was removed under reduced pressure. 125-127 g of acid (96% of theory) were obtained as a colorless liquid; Example 2; A reaction vessel was charged with dimethylformamide (406 ml, 382 g) and sodium methoxide (140 ml, 136 g, 753 mmol, a 30% solution in methanol). The reaction mixture was heated to 600C. Dimethyl isopropylmalonate (127 ml, 131 g, 753 mmol) was metered in within thirty minutes, and methanol was distilled off at a temperature of 69-74C and a pressure of 330-50 mbar. frans-1 ,3-Dichloropropene (70 ml, 84 g, 753 mmol) was metered in at 800C within one hour and the reaction solution was stirred at 8O0C for ninety minutes.CaCb (83.5 g, 753 mmol) was added and the mixture was heated to 140-1450C. Methanol was metered in continuously (a total of 30 ml, 24 g, 742 mmol), in the course of which the reaction temperature was kept at approx. 140-1450C. The suspension is stirred at this temperature for 12 hours, in the course of which gas (mainly CH3CI and CO2) formed. The maximum amount of gas in the first half hour was approx. 6 liters.Dimethylformamide (260 ml, 247 g) was distilled off at 70-800C and a pressure of (150 – 25 mbar). The resulting suspension was cooled to 55C, and admixed with 250 g of water, 90 g of HCI (a 34% aqueous solution) and 190 g of MTBE. The phases were separated and the organic phase was washed with 100 g of water. The organic phase thus obtained was worked up as follows: EPO The organic MTBE phase was concentrated under reduced pressure. The remainder of MTBE was removed by adding 50 g of water and distilling off an MTBE/water mixture.Water (135 g) and sodium hydroxide solution (75 g, 49 ml, a 50% aqueous solution) were added, and the reaction solution was heated at a pressure of max. 3 bar and 105-1100C for two hours. On completion of reaction, approx. 60 ml of an MeOH/water mixture were distilled off. Thereafter, water (135 g) was added and adjusted to pH 3.0-4.0 with H2SO4 (76% aqueous solution). The solution was admixed with isopropyl acetate at 25C and the phases were separated. The organic phase was washed with 30 g of water and the solvent was removed under reduced pressure. 191 g of racemic acid were obtained as brownish liquid (92% of theory).The organic MTBE phase was extracted with water (25 g) and sodium hydroxide solution (10 g, 50% aqueous solution), and then washed with water (25 g). The combined aqueous phases contained 17 g of rac. acid (13% of theory) which can be esterified with MeOH and catalytic amounts of H2SO4.The organic phase was concentrated under reduced pressure and the residue was distilled at 170-1710C and standard pressure. 113 g of rac. ester were obtained as a colorless liquid (79% of theory).

The synthetic route of Dimethyl Isopropylmalonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DSM FINE CHEMICALS AUSTRIA NFG GMBH & CO KG; WO2007/17018; (2007); A1;,
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