Month: December 2020

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. 2178-24-7, name is Ethyl (2-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2178-24-7

b) 4-(alpha-Ethoxycarbonyl-benzyloxy)benzyl alcohol 41.8 g (0.172 mol) of ethyl 2-bromo-phenylacetate and 21.3 g (0.172 mol) of 4-hydroxybenzyl alcohol are dissolved in 850 ml of acetone and 24.8 g (0.18 mol) of potassium carbonate and 5.0 g (0.03 mol) of potassium iodide are added thereto. The reaction mixture is refluxed for 60 hours with stirring. Then the inorganic salts are filtered off and the residue is washed with hot acetone. The filtrate is evaporated down and the residue is purified over a silica gel column (particle size: 0.063-0.02 mm), initially using petroleum ether as eluant and then using mixtures of petroleum ether and ethyl acetate of increasing polarity (9:1, 8:2 and 7:3). The unified fractions are evaporated down in vacuo. Yield: 30.65 g (62.5% of theory), Rf value: 0.40 (silica gel; eluant: ethyl acetate/petroleum ether=3:7)

The synthetic route of 2178-24-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dr. Karl Thomae GmbH; US5519138; (1996); A;,
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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 2475-80-1 as follows. 2475-80-1

EXAMPLE 52 2′-Carboxy-4′-methoxyoxanilic acid 1-ethyl 2′-methyl ester. 58 6-Amino-m-anisic acid methyl ester (4.7 g, 0.0283 mole) is condensed with 3.48 ml (0.0311 mole) of ethyl oxalyl chloride in a manner similar to example 3, giving 5.27 g of the title compound, m.p. 129-133C., after crystallization from ethanol. Elemental Analysis for C13 H15 NO6: Calc’d: C, 55.51; H, 5.38; N, 4.98. Found: C, 55.72; H, 5.38; N, 5.37.

According to the analysis of related databases, 2475-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US3966965; (1976); A;,
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214262-88-1, Adding a certain compound to certain chemical reactions, such as: 214262-88-1, name is Methyl 2-(2-chloro-4-fluorophenyl)acetate, 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 214262-88-1.

Example 25. 2-(2-chloro-4-fluorophenyl)- 6-methoxy -8-(6-methyl-7-oxo-6,7-dihydro- -pyrrolo[2,3-c]pyridin-4-yl)-2H-l,4-benzoxazin-3(4H)-one A solution of methyl (2-chloro-4-fluorophenyl)acetate (100 mg, 0.5 mmol) (Acros Organics cat 30478) and N-bromosuccinimide (90 mg, 0.5 mmol) in carbon tetrachloride (0.7 mL) was heated to 100 C for 1 h. The reaction mixture was cooled to room temperature, filtered, and partitioned between ethyl acetate and water. The combined organic layers were washed with brine, dried over MgSC , filtered, and concentrated to afford crude methyl bromo(2-chloro-4-fluorophenyl)acetate as light yellow semi solid (120 mg, 90%).

According to the analysis of related databases, 214262-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; COMBS, Andrew, P.; MADUSKUIE, Thomas, P., Jr.; FALAHATPISHEH, Nikoo; WO2015/164480; (2015); A1;,
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2905-65-9, Adding some certain compound to certain chemical reactions, such as: 2905-65-9, name is Methyl 3-chlorobenzoate, 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 2905-65-9.

General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ¡À 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ¡À 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized. 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 2905-65-9. Reference:
Article; Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil; Synthesis; vol. 48; 17; (2016); p. 2795 – 2807;,
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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. 10602-06-9, name is Methyl 3-ethynylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 10602-06-9

General procedure: Azide 13 (300 mumol), alkyne (750 mumol), CuSO4 (9.6 mg, 60 mumol) and sodium ascorbate (60.0 mg, 300 mumol) were dissolved in 1:1 t-BuOH/H2O (3 mL). The mixture was stirred for 2 h at rt. After the completion of the reaction, the mixture was filtered and washed with H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 * 70 mL). The combined organic extracts were dried over anhyd MgSO4, filtered, and concentrated by rotary evaporation (residue B). The solid A and residue B were combined and purified by column chromatography to afford 8 or 9.

The synthetic route of 10602-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Doohee; Park, Yunjeong; Yoon, Jieun; Aman, Waqar; Hah, Jung-Mi; Ryu, Jae-Sang; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4855 – 4866;,
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73792-08-2, These common heterocyclic compound, 73792-08-2, name is Methyl 4-amino-2-fluorobenzoate, 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 solution of the compound of Reference Example 11-1 (358 mg, 1.20 mmol) in dichloromethane (4 mL), oxalyl chloride (113 muL, 1.32 mmol) and DMF (5 muL) were added at 0C, and the mixture was stirred for 20 minutes. To the reaction solution, a solution of methyl 4-amino-2-fluorobenzoate (105.4 mg, 0.623 mmol) and diisopropylethylamine (310 muL, 1.80 mmol) in dichloromethane (2 mL) was added at 0C, and the mixture was stirred for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated saline solution, then dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the title compound (83.2 mg, 30%). MS (ESI+) 449 (M+1, 84%)

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 73792-08-2.

Reference:
Patent; Sumitomo Dainippon Pharma Co., Ltd.; IKUMA Yohei; FUKUDA Nobuhisa; IWATA Masato; KIMURA Hidenori; SUZUKI Kuniko; EP2876105; (2015); A1;,
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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. 23680-40-2 name is Methyl 3-bromopropiolate, 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. 23680-40-2

Reaction Step 2. Synthesis of 7-tert-butyl 2-ethyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylateA mixture of methyl 3-bromopropiolate (5.00 g, 28.2 mmol, 1.0 eq) and tert-butyl 1H-pyrrole-1-carboxylate (14.00 g, 84.7 mmol, 3.0 eq) in a sealed tube was heated to 90 C. for 14 h. After completion of the reaction (monitored by TLC, 5% ethyl acetate-hexane Rf=0.3), The reaction mixture was purified without work up by flash column chromatography on silica gel (100-200 mesh), eluting with 5% ethyl acetate in hexanes to afford 7-tert-butyl 2-methyl 3-bromo-7-azabicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylate (2.0 g, 20%) as a brown oil. LCMS m/z=344.2 (M+1); purity=75%.

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

Reference:
Patent; INNOV17 LLC; Gaweco, Anderson; Tilley, Jefferson; Blinn, James; US2015/252051; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2065-23-8, 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. 2065-23-8, name is Methyl 2-phenoxyacetate, A new synthetic method of this compound is introduced below.

REFERENCE EXAMPLE 90 Dimethyl 2-oxo-3-phenoxy-propylphosphonate 90 STR109 Dimethyl methylphosphonate (18 ml, 0.166 mol) was addded to anhydrous THF (150 ml) under argon atmosphere and cooled to -78 C. After 20 min. a solution of n-butyl lithium in hexane (1.59N, 108.8 ml, 0.173 mmol) was added to the mixture. After being stirred for 30 min. a solution of methyl phenoxyacetate (10 ml, 0.069 mmol) in 10 ml of anhydrous THF was added, and the reaction mixture was stirred successively for 30 min. at -78 C. and for 30 min. at room temperature, and acidified with acetic acid. After confirming a weakly acidic pH of the solution thus obtained, THF was distilled out. Water (50 ml) was added to the residue, and the resulting mixture was extracted with ethyl acetate (150 ml*3). The combined organic layers were washed with 100 ml of water and with 100 ml of brine, dried over anhydrous sodium sulfate, and concentrated. The oily product was distilled under reduced pressure to afford dimethyl 2-oxo-3-phenoxypropylphosphonate (14.65 g, 0.057 mol, yield: 82.3%). B.p.: 145-147 C./0.1 mmHg. The product was identified by the following data. IR(liquid film): 3450, 3070, 3025, 2960, 2920, 2860, 1740, 1605, 1595, 1495, 1460, 1430, 1405, 1370, e1300, 1250, 1230, 1180, 1160, 1100, 1030, 890, 830, 810, 800 cm-1. NMR(90 MHz, CDCl3, delta): 3.27(2H, d, J=22.7 Hz); 3.77(6H, d, J=11.2 Hz); 4.69(2H, s); 6.84-7.38 (5H, m).

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; Toray Industries, Inc.; US4775692; (1988); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 59833-69-1 as follows. 59833-69-1

General procedure: To a stirred solution of 12e (62 mg, 0.4 mmol) in CH2Cl2 (5 mL) were added a solution of 18 (133 mg, 0.4 mmol) in CH2Cl2 (3 mL) and then pyridine (0.067 mL, 0.8 mmol). After stirring overnight at room temperature, the reaction mixture was diluted with water and extracted with EtOAc (¡Á2). The combined organic layers were washed with 1 M NaOH aq, water, brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to yield methyl ester (120 mg, 63%); TLC Rf = 0.14 (n-hexane/EtOAc, 7:3); 1H NMR (300 MHz, CDCl3) delta 7.60-7.38 (m, 4H), 7.32 (t, J = 7.8 Hz, 1H), 7.06 (d, J = 7.5 Hz, 1H), 6.92-6.77 (m, 4H), 6.74-6.66 (m, 2H), 4.70-4.60 (m, 1H), 4.26 (dd, J = 9.6, 5.4 Hz, 1H), 4.14 (dd, J = 11.4, 6.6 Hz, 1H), 3.71 (s, 3H), 3.65 (s, 2H), 3.39 (dd, J = 11.4, 3.0 Hz, 1H), 3.26 (dd, J = 11.4, 7.8 Hz, 1H), 2.91 (s, 3H), 2.51 (s, 3H).CommentTo a stirred solution of methyl ester (120 mg, 0.25 mmol) described above in MeOH (4 mL) and THF (4 mL) was added 5 M NaOH aq (2 mL). After stirring for 1 h at room temperature, the reaction mixture was diluted with 2 M HCl aq and extracted with EtOAc (¡Á2). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated in vacuo to give a crude product, which was washed with EtOAc/n-hexane to yield 4a (85 mg, 73%) as a pale blue powder

According to the analysis of related databases, 59833-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwahashi, Maki; Takahashi, Eiji; Tanaka, Motoyuki; Matsunaga, Yoko; Okada, Yutaka; Matsumoto, Ryoji; Nambu, Fumio; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5361 – 5371;,
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Ester – an overview | ScienceDirect Topics

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. 36692-49-6, name is Methyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 36692-49-6

Step 450b. The mixture of (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (5 g, 23.2 mmol) in acetonitrile (40 mL) was added 1,1?-carbonyldiimidazole (3.95 g, 24.5 mmol). The resulting mixture was stirred at room temperature for 20 min before being added methyl 3,4-diaminobenzoate (3.86g, 23.2 mmol). The solution was stirred at room temperature for another 3 hours before being partitioned between water and EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated to afford a brown slurry, which was purified by flash column chromatography (silica, hexane-EtOAc) to give the desired product as a light yellow oil (8.14g, 98%). ESIMS m/z=364.17 [M+H]+. ; Step 450c. The solution of compound from step 450b in acetic acid (150 mL) was stirred at 60 C. for three days before all volatiles were removed. The resulting residue was partitioned between aqueous NaHCO3 and EtOAc. The organic phase was separated, dried (Na2SO4) and concentrated to afford a brown oil, which was purified by flash column chromatography (silica, hexane-EtOAc) to give the desired product as a light yellow solid (2.02 g, 28%). ESIMS m/z=346.15 [M+H]+.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Enanta Pharmaceuticals, Inc.; Qiu, Yao-Ling; Wang, Ce; Peng, Xiaowen; Ying, Lu; Or, Yat Sun; US2020/2314; (2020); A1;,
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