Category: esters-buliding-blocks

Synthetic Route of 18013-97-3, 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. 18013-97-3, name is Diethyl 2,5-dibromoterephthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2 Diethyl 2,5-di(benzo[b]thiophen-4-yl)terephthalate To a mixture of magnesium turnings (0.91 g, 36 mmol) and anhydrous tetrahydrofuran (20 cm3) is added 4-bromobenzo[b]thiophene (7.0 g, 33 mmol) and the mixture heated at 75 C. for 17 hours. The resulting suspension is syringed into a solution of tributyltinchloride (16 g, 49 mmol) in anhydrous tetrahydrofuran (20 cm3) at -78 C. The ice bath is removed and the resulting mixture is stirred at 23 C. for 17 hours. The reaction mixture is quenched with water (100 cm3) and extracted with 40-60 petroleum (5*50 cm3). The combined organic phase is washed with brine (50 cm3), dried over magnesium sulphate, filtered and the solvent removed in vacuo to give crude (4-tributylstannanyl-benzo[b]thiophen-2-yl). Nitrogen gas is bubbled for an hour through a suspension of 2,5-dibromo-terephthalic acid diethyl ester (2.3 g, 6.0 mmol) in anhydrous N,N-dimethylformamide (50 cm3) and tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol) and tri(o-tolyl)phosphine (0.2 g, 0.6 mmol) are added. The resulting mixture is heated to 90 C. and the prepared (4-tributylstannanyl-benzo[b]thiophen-2-yl) is added. The reaction mixture is stirred at 90 C. for 17 hours. The reaction mixture is concentrated in vacuo and purified using silica gel column chromatography (gradient of 40-60 petroleum to diethyl ether) to give diethyl 2,5-di(benzo[b]thiophen-4-yl)terephthalate (0.9 g, 31%) as a white solid. 1H NMR (300 MHz, CDCl3) 8.05 (2H, s, ArH), 7.95 (2H, d, ArH, J 8.0), 7.49-7.44 (4H, m, ArH), 7.37 (2H, d, ArH, J 5.5), 7.28 (2H, d, ArH, J 5.5), 3.92 (4H, q, CH2, J 7.2), 0.72 (6H, t, 2CH3, J 7.2).

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, Diethyl 2,5-dibromoterephthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; D’Lavari, Mansoor; Mitchell, William; Wang, Changsheng; Tierney, Steven; Sparrowe, David; US2015/144847; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 25081-39-4,Some common heterocyclic compound, 25081-39-4, name is Methyl 3,5-dimethylbenzoate, molecular formula is C10H12O2, 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 CC: (R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one To a solution of (R)-4-methyldihydrofuran-2-one (1.68 g in 40 mL dioxane) were added 5.51 g 3,5-dimethylbenzoic acid methyl ester followed by 1.82 g sodium hydroxide and the mixture heated to reflux on an oil bath. After 3 hours, the mixture was cooled to room temperature and the pH neutralized by the addition of 0.5N hydrochloric acid. The mixture was then extracted with ethyl acetate and the organic portion washed with brine and diied over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 9:1) gave the title compound (2.42 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3,5-dimethylbenzoate, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; US6211224; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3377-20-6, name is Diethyl 2-methylenemalonate, molecular formula is C8H12O4, 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: Diethyl 2-methylenemalonate

nBuLi solution (2.5 M in hexanes, 2.2 mL, 5.5 mmol) was added, dropwise over 2 min., to a cooled (-20 C bath maintained by an immersion cooler) solution of N,N,N?-trimethylethylenediamine (587 mg, 5.74 mmol) in 2-MeTHF (13 mL). After stirring for 15 min., 1- naphthaldehyde (813 mg, 5.21 mmol) was added dropwise via syringe by mass difference over 1-2 min. After 15 min., more nBuLi solution (2.5 M in hexanes, 6.2 mL, 16 mmol) was added, dropwise over 5 min. After stirring at this temperature for 24 h, the reaction mixture was cooled in a dry ice/acetone bath. Diethyl ketomalonate (3.46 mL, 22 mmol) was then added to the rxn. mixture, dropwise over 5 min. After 5 min., the reaction was quenched by rapid addition of 10. % aq. NH4Cl, and cooling was ended. The resulting mixture was partitioned between dichloromethane and brine. The aqueous layer was extracted once more with dichloromethane, and the combined organic layers were dried (sodium sulfate) and evaporated to afford a yellow oil that darkened over time. Chromatographic purification (144 g silica gel, heptane to 3:7 EtOAc/heptane gradient) afforded the title compound as a mixture with an amine side product.2 The chromatography fractions containing the title compound were washed with 1.0 M aq. HCl and brine, dried (sodium sulfate), and evaporated to afford the title compound as a clear, yellow oil (503 mg, 29 % yield, ca. 85 % purity). LCMS (ESI) m/z: 353.1 [M+Na] (48 %). 1H NMR (400 MHz, CDCl3) delta 1.31 (t, J = 7.1 Hz, 3H), 1.36 (t, J = 7.1 Hz, 3H), 2.50 (s, 1H), 4.26 (dq, J = 10.8, 7.1 Hz, 1H), 4.34 (dq, J = 10.8, 7.1 Hz, 1H), 4.38 (dq, J = 10.7, 7.1 Hz, 1H), 4.42 (dq, J = 10.7, 7.1 Hz, 1H), 6.38 (s, 1H), 7.27 (d, J = 8.9 Hz, 1H), 7.39 (ddd, J = 8.2, 6.9, 1.2 Hz, 1H), 7.55 (ddd, J = 8.3, 6.9, 1.3 Hz, 1H), 7.80-7.88 (m, 2H), 7.94 (d, J = 8.3 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3377-20-6, its application will become more common.

Reference:
Article; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 57486-69-8, A common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, molecular formula is C9H9BrO2, 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 A. [4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester. A mixture of 1-(2-fluoro-4-nitro-phenyl)-piperazine (4.0 g, 18 mmol), methyl alpha-bromophenyl acetate (2.9 mL, 18 mmol) and K2CO3 (3.0 g, 21 mmol) in DMF (40 mL) was stirred at rt for 18 h. The reaction mixture was poured into H2O (150 mL) and extracted with EtOAc (2*). The combined organic layers were washed with 0.5 N HCl and brine, dried (Na2SO4), and concentrated to give an orange solid (6.5 g, 98%). MS (ESI): mass calcd. for C19H20FN3O4, 373.38; m/z found, 374.4 [M+H]+. 1H NMR (CDCl3): 7.98-7.95 (m, 1H), 7.89-7.86 (dd, J=13.1, 2.6, 1H), 7.45-7.43 (m, 2H), 7.39-7.34 (m, 3H), 6.87 (t, J=8.8, 1H), 4.09 (s, 1H), 3.71 (s, 3H), 3.33-3.31 (m, 4H), 2.66-2.64 (m, 4H). Step A. [4-(2-Fluoro-4-nitro-phenyl)-piperazin-1-yl]-phenyl-acetic acid methyl ester. The title compound was prepared using methods similar to those described in Example 44, Step A.

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; Bonaventure, Pascal; Carruthers, Nicholas I.; Chai, Wenying; Dvorak, Curt A.; Jablonowski, Jill A.; Rudolph, Dale A.; Seierstad, Mark; Shah, Chandravadan R.; Swanson, Devin M.; Wong, Victoria D.; US2007/100141; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 106614-28-2, name is Methyl 2,4-difluorobenzoate, molecular formula is C8H6F2O2, 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. Recommanded Product: 106614-28-2

Example 43C methyl 2-(1H-pyrrolo[2,3-b]pyridin-5-yloxy)-4-fluorobenzoate A mixture of EXAMPLE 43B (8.5 g), methyl 2,4-difluorobenzoate (7.05 g), and K3PO4 (9.32 g) in diglyme (40 mL) at 115 C. was stirred for 24 hours. The reaction was cooled, diluted with ether (600 mL), and washed twice with water, and brine, and concentrated. The crude product was chromatographed on silica gel with 2-50% ethyl acetate/hexanes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 106614-28-2, its application will become more common.

Reference:
Patent; ABBOTT LABORATORIES; US2010/184766; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, A new synthetic method of this compound is introduced below., SDS of cas: 150529-73-0

(3-Bromophenyl)acetic acid 11 (5.0 g, 23.3 mmol) and methanol (50 mL) were refluxed for 3 h in the presence of 0.2 mL of concentrated hydrochloric acid (HCl) to give the methyl (3-bromophenyl)acetate. After neutralization with saturated NaHCO3 and washing with brine, a pure product was obtained from the diethyl ether extract. This methyl acetate (4.9 g, 21.4 mmol) in dry THF (35 mL) was added dropwise to a stirred solution of 2.0 mol/L lithium diisopropylamide (LDA) (12.9 mL, 25.8 mmol) in THF/ethylbenzene/heptane at -78 C under argon (Ar), and after 30 min, iodomethane (CH3I) (2.0 mL, 32.2 mmol) was added slowly. The resulting solution was stirred for 5 h with the temperature changed from -78 to -40 C, then evaporated to dryness, and extracted with CH2Cl2 (50 mL). Evaporation of the solvent and purification of the residue by silica gel chromatography (n-hexane/AcOEt, 20:1) yielded the title compound as a colorless liquid (77.2%). 1H NMR (CDCl3) delta: 1.49 (3H, d, J = 7.1 Hz, alpha-CH3), 3.67 (3H, s, CO2CH3), 3.68 (1H, q, J = 7.1 Hz, CH), 7.18 (1H, t, J = 7.5 Hz, Ar-H5), 7.23 (1H, dt, J = 7.8, 1.7 Hz, Ar-H6), 7.38 (1H, dt, J = 7.3, 1.8 Hz, Ar-H4), 7.44 (1H, st, J = 1.7 Hz, Ar-H2). FAB-MS (m/z): 243.02 (M++H, calcd for C10H1279BrO2: 243.00).

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:
Article; Yamakawa, Naoki; Suemasu, Shintaro; Matoyama, Masaaki; Tanaka, Ken-Ichiro; Katsu, Takashi; Miyata, Keishi; Okamoto, Yoshinari; Otsuka, Masami; Mizushima, Tohru; Bioorganic and Medicinal Chemistry; vol. 19; 11; (2011); p. 3299 – 3311;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 7364-20-7, 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. 7364-20-7, name is Methyl 4-ethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Hydrazine hydrate 64% (v/v) (30.0 mL, 0.33 mol) was heated up to 50-60 C. The methyl ester 3 (0.01 mol) was added and the mixture was heated at reflux for 10 min. The cooling was performed sequentially in water bath, followed by ice bath and dry ice-ethanol bath. The precipitate was filtered and washed with cold water.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-ethylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ishii, Marina; Jorge, Salomao Doria; De Oliveira, Alex Alfredo; Palace-Berl, Fanny; Sonehara, Ieda Yuriko; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa; Bioorganic and Medicinal Chemistry; vol. 19; 21; (2011); p. 6292 – 6301;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14273-90-6, name is Methyl 6-bromohexanoate, 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 14273-90-6, name: Methyl 6-bromohexanoate

General procedure: A solution of racemic norketamine (23) (0.4 g, 1.78 mmol), methyl2-bromoacetate (0.32 g, 2.14 mmol), KI (0.089 g, 0.54 mmol), K2CO3(0.74 g, 5.35 mmol) in MeCN (10 mL) was heated to a 100 °C in sealedtube for 12 h. The reaction mixture was cooled to room temperature,filtered and the solvent evaporated. The residue was purified by columnchromatography on silica gel eluting with EtOAc/hexanes (0?35percent) togive 2 (0.42 g, 80percent) as pale yellow oil. This was dissolved in Et2O(5 mL), cooled to 0 °C, and HCl in Et2O (2 M, 2.11 mmol) was addeddropwise. The solvent was evaporated under reduced pressure, the residuewas taken up in EtOAc (1 mL) and sonicated at room temperaturefor 2 min. The white precipitate was diluted with EtOAc (5 mL), filteredwashed with EtOAc and dried under vacuum to give

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:
Article; Dimitrov, Ivaylo V.; Harvey, Martyn G.; Voss, Logan J.; Sleigh, James W.; Bickerdike, Michael J.; Denny, William A.; Bioorganic and Medicinal Chemistry; vol. 27; 7; (2019); p. 1226 – 1231;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl methyl malonate

To a solution of sodium hydride (4.60 g, 115 mmol) in DMSO (120 mL) was added tert-butyl methyl malonate dropwise. The resulting solution was heated to 100°C for 30 min then cooled to room temperature, where 3-cyano-4-fluorobenzotriflulide (9.86 g, 52.0 mmol) was added and the reaction reheated to 100°C. After 2 h the reaction was cooled to room temperature and poured into a mixture of saturated aqueous ammonium chloride (400 mL), EA (100 mL) and hexanes (100 mL). The organic layer was separated and washed once with saturated aqueous ammonium chloride, three times with water and once with brine. Filtration through a short plug of silica gel, followed by concentration under reduced pressure gave a crude yellow oil. This product was dissolved in ethyl alcohol (50 mL), treated with Raney Nickel (-1 g), and placed on a Parr shaker under 50 psi H2. After 18 h the reaction was filtered through celite and concentrated under reduced pressure to give 12.5 g of product (76 percent). ESI-MS calc. for C15H16F3N03 : 315; found 631 (2M+H). H NMR (CDC13, 500 MHz) 8 7.60 (d, J = 10.0 Hz, 1H), 7.50 (s, 1H), 7.44 (d, J = 10.0 Hz, 1H), 7.24 (bs, 1H), 4.86 (d, J = 14. 5 Hz, 1H), 4.46 (t, J = 14.5 Hz, 2H), 2.20 (bs, 1H), 1.45 (bs, 9H).

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; MERCK & CO., INC.; MERCK SHARP & DOHME LIMITED; WO2003/93231; (2003); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 82702-31-6, 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 82702-31-6 as follows.

Cesium carbonate (3.1 g, 9.6 mmol) was added to 4-fluoro-2,6-dimethylphenol (0.9 g, 6.4 mmol) and methyl 3-bromo-4-fluorobenzoate (1.57 g, 6.7 mmol) ) in a solution of dimethyl sulfoxide (10 mL). The reaction mixture was stirred at 80 C for 12 hr, then cooled to room temperature, then water (50mL), ethyl acetate (50mL*2). The organic phase was washed with brine (25 mL*4) and evaporated to dryness. The crude product was separated by column ( petroleum ether: ethyl acetate = 20:1) to give methyl 3-bromo-4-(4-fluoro-2,6-dimethylphenoxy) benzoate (1.4 g, yield 62%).

According to the analysis of related databases, 82702-31-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Jiangsu Haosen Pharmaceutical Group Co., Ltd.; Ye Guozhong; Liu Lei; Bao Rudi; Wu Shenghua; Deng Haining; (130 pag.)CN110041253; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics