Tag: M.W=200-300

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;,
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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;,
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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: 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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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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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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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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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;,
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Reference of 55666-43-8, 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. 55666-43-8 name is tert-Butyl 3-bromopropanoate, 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.

The methodologies described in Example 36 substituting feri-butyl 3-bromopropanoate for 2-bromoethanol and additionally including acetone (0.4 mL) in the solution gave the title compound. MS (ESI+) m/z 554 (M+H)+.

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

Reference:
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; CHUNG, Seungwon; ZHANG, Qingwei, I.; SHI, Lei; MURAUSKI, Kathleen; DART, Michael, J.; RANDOLPH, John, T.; (238 pag.)WO2019/90085; (2019); A1;,
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