Month: June 2021

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;,
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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;,
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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. 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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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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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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