Month: May 2021

Electric Literature of 139911-28-7, 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. 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 2a. 8-fluorophenanthridin-6-ol.A mixture of methyl 2-bromo-5-fluorobenzoate (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80 C for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromo-5-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; ABBOTT LABORATORIES; MCDANIEL, Keith, F.; CHEN, Hui-ju; SHANLEY, Jason, P.; GRAMPOVNIK, David, J.; GREEN, Brian; MIDDLETON, Timothy; HOPKINS, Todd; OR, Yat, Sun; WO2012/92411; (2012); A2;,
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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. 1731-79-9, name is Dimethyl dodecanedioate, A new synthetic method of this compound is introduced below., SDS of cas: 1731-79-9

1,12-dodecanedioic acid dimethyl ester (1000.0g, 3.87 mols) was put into a reactor, heated and stirred under a reduced pressure of 80kPa at 105C. Methanol was distilled off while the mixture of gamma-butyrolactone (83.3g, 0.97 mol) and 28% by weight of sodium methoxide solution in methanol (186.7g, 0.97 mols) prepared at the room temperature was dropped into the heated 1,12-dodecanedioic acid dimethyl ester in 30 minutes. After continuing the reaction for 30 minutes then, the pressure was reduced to 26.7 kPa to further continue the reaction for 240 minutes. Next, after returning to ordinary pressure, the reactant was cooled to 70C and, while being stirred, methyliodide (137.7g, 101.6 mols) was dropped into it in 30 minutes. N-hexane (700g) and, next, water (3009) were poured into it. After removing the water layer, it was washed with aqueous solution of 10% sodium hydroxide (150g: twice) and water (200.0g: twice). N-hexane was distilled off under a reduced pressure. The remained oily substance was subjected to a distillation under a reduced pressure (oil bath temperature 200C/60 to 130Pa) and excessive 1,12-dodecanedioic acid dimethyl ester was distilled off. 762.9g of a distilled substance and 264.2g of a distillation residue were obtained. As a result of an analysis of the distillation residue by gas chromatography, it was found that 80.7% by weight of the compound indicated by the general formula (2) (n = 10, R = Me) was contained. This was mixed with aqueous solution of 10% sodium hydroxide (675g) and heated/refluxed for 5.5 hours. After diethylene glycol (230g) and 60% hydrazine monohydrate (124g) were added to the reaction liquid and stirred for one hour at 110C, the temperature of the reaction system was elevated to 170 to 200C while removing water, and after aqueous solution of 30% sodium hydroxide (100g) was dropped into it in 4 hours, it was stirred for 6 hours at that temperature. While pouring water (930g) into it, it was cooled, and with addition of diluted sulfuric acid it was extracted with toluene. After the organic layer was washed with water, the solvent was removed under a reduced pressure, and 254g of a crystalline residue containing 13-methyl-15-hydroxypentadecanoic acid (n = 10) as the main component was obtained. This was cyclized by intramolecular ester interchange reaction to thereby obtain 80.7g of a cyclic compound. This contained 98.9% by weight of 13-methyl-15-pentadecanolide. The yield was 32 mol%/butyrolactone. 1H-NMR(CDCl3,400MHz) 4.16(2H)m; 2.32(2H)m; 0.90(3H)d J=6.4Hz 13C-NMR(CDCl3) 173.89; 61.86; 35.31; 34.49; 34.20; 30.82; 27.68; 27.25; 26.57; 26.42; 26.26; 26.10; 25.87; 24.89; 24.52; 19.51 IR(film) 2930; 2860; 1740; 1460; 1350; 1245; 1173; 1115 MS 254(5); 236(9); 225(11); 207(21); 111(16); 97(35); 83(42); 70(100); 55(68); 41 (40)

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; SODA AROMATIC COMPANY, LIMITED; EP1741706; (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. 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H7Cl2NO2

(i) Sodium nitrite (20 g) in water (50 ml) was added to a stirred mixture of methyl 4-amino-3,5-dichlorobenzoate (6.23 g) in concentrated sulphuric acid (110 g) and water (95 ml) at 0C. The mixture was stirred until all the solid had dissolved (overnight at 0C). To the stirred solution was added a solution of potassium iodide (25 g) in water at 50C and the resulting mixture was stirred at 20C overnight. The mixture was extracted with diethyl ether. The ethereal extracts were washed with aqueous sodium bisulphite solution and then dried over anhydrous magnesium sulphate. The solvent was evaporated in vacuo and the residue was chromatographed on silica, eluding with hexane: dichloromethane 7:3. 3.75 g of methyl 3,5-dichloro-4-iodobenzoate was obtained. Nuclear magnetic resonance spectrum (NMR) was as follows: ‘H (ppm from TMS in CDCl3, integral, number of peaks): 3.90, 3H, s; 7.95, 2H, s. Mass spectrum M+1 331.

The synthetic route of 41727-48-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE WELLCOME FOUNDATION LIMITED; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; EP279698; (1990); A3;,
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These common heterocyclic compound, 6642-30-4, name is Methyl methylcarbamate, 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. name: Methyl methylcarbamate

Step A 6-Cyanoindazole A solution of sodium nitrite (218 mg, 3.16 mmol) in water (1 mL) was added dropwise over 2 min to a stirred suspension of 3-amino-6-cyanoindazole (250 mg, 1.58 mmol) in water (1 mL) and acetic acid (2 mL) at 0 C. The resulting thick suspension was warmed to rt. After 16 h the mixture was cooled to 0 C. and the solids were collected by filtration, washing with cold water. The solids were suspended in 0.1 M HCl (4 mL), DME (3 mL) was added and the resulting mixture was stirred and heated to 80 C. for 1.5 h. The reaction was cooled and concentrated to 1/3 the volume. The residue was neutralised with sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography on silica (5:1 chloroform/ethyl acetate) to give the title compound as a yellow solid: LRMS=143.1 (M)+; 1H NMR (CDCl3) delta 7.39 (dd, J=1.1 and 8.3 Hz, 1H), 7.87 (dd, J=0.9 and 8.3 Hz, 1H), 7.94 (dd, J=0.9 and 2.1 Hz, 1H), 8.21 (d, J=0.9 Hz, 1H).

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

Reference:
Patent; Merck & Co., Inc.; US6376499; (2002); B1;,
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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 210530-71-5 as follows. Recommanded Product: Methyl 2-(3,4-difluorophenyl)acetate

Sodium hydride (containing mineral oil at 40%, 0.48 g) was added to a solution of methyl (3,4-difluorophenyl)acetate (CAS No.210530-71-5, 2.04 g) in DMF (30 mL) at 0 C., and the reaction solution was stirred at room temperature for 10 minutes. 1-chloro-3-iodopropane (1.3 mL) was added to the reaction solution at 0 C., and the reaction solution was stirred at room temperature for two hours. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The resulting extract washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. Hydrazine monohydrate (5.5 g) was added to a solution of the resulting residue in ethanol (50 mL) at room temperature, and the reaction solution was stirred at 80 C. for seven hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the residue, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent:heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 1.42 g of the title compound. The property values of the compound are as follows. ESI-MS; m/z 227 [M++H]. 1H-NMR (CDCl3) delta (ppm): 1.84-2.06 (m, 3H), 2.10-2.21 (m, 1H), 3.53-3.71 (m, 3H), 4.59 (brs, 2H), 6.89-6.95 (m, 1H), 6.97-7.05 (m, 1H), 7.06-7.26 (m, 1H).

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eisai R&D Management Co., Ltd.; US2007/219181; (2007); A1;,
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2905-69-3, name is Methyl 2,5-dichlorobenzoate, 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. SDS of cas: 2905-69-3

Add 19.1 g of 2,5-dichlorobenzoic acid (0.1 mol) and 120 ml of methanol to the reaction flask.Add a catalytic amount of acid and reflux at 65~70 C for 8 hours.After the reaction, the excess methanol was distilled off under reduced pressure.19.2 g of methyl 2,5-dichlorobenzoate was obtained in a yield of 93.6%.The obtained methyl 2,5-dichlorobenzoate (0.094 mol) was added to the reaction flask.Add 30 g of bromine (0.19 mol) and 2.5 g of aluminum tribromide.The reaction was carried out at 50 C for 6 hours, and after the reaction was completed, it was extracted with ethyl acetate and water.After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give 24 g of Compound 3.The yield was 90.2%.Adding the obtained compound 3 to the reaction flask,Add 60 ml of methanol and a suitable palladium catalyst and react at 80 C for 6 hours.The reaction was extracted, dried, and the solvent was evaporated under reduced pressure to give 17.1 g of Compound 4.The yield was 86%.Finally, the compound 4 was placed in a reaction flask, 100 ml of deionized water was added, and an appropriate amount of acid was added, and the reaction was carried out at 60 C for 3 hours. After the reaction was completed, it was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The final product, dicamba, 14.5 g was obtained after pressure distillation.The total yield is 65%.

The synthetic route of 2905-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Changqing Agrochemical Co., Ltd.; Yu Guoquan; Sun Xialin; Ma Changqing; Ding Huaping; (6 pag.)CN109134232; (2019); A;,
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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. 40637-56-7, name is Dimethyl 2-allylmalonate, A new synthetic method of this compound is introduced below., COA of Formula: C8H12O4

4.1.1 2-Allyl-2-methoxycarbonyl-malonic acid dimethyl ester (5) 13 At 0 C, to a suspension of NaH (60% in mineral oil) (5.85 g, 146.2 mmol, 1.5 equiv) in THF (150 mL), was added 4 (16.78 g, 97.4 mmol) and the mixture was warmed to rt and stirred during 1 h. Then, freshly distilled ClCO2Me (20 mL, 258.0 mmol, 2.6 equiv) was slowly added at 0 C and the solution was warmed to rt and stirred during 2 h. The reaction mixture was diluted in diethyl ether and washed with saturated aqueous solution of ammonium chloride and brine, dried over MgSO4, filtered, and concentrated. Pure compound 5 (20.41 g, 88.6 mmol, 91%) was obtained as a colorless oil. 1H NMR (CDCl3, 200 MHz) delta 5.95-5.77 (ddt, J=17.2; 10.3 and 7.4 Hz, 1H, H2C=CHCH2); 5.09 (dd, J=17.2 and 1 Hz, 1H, HC=CHtrans); 4.99 (dd; J=10.3 and 1 Hz, 1H, HC=CHcis); 3.70 (s, 9H, CO2CH3); 2.78 (d, J=7.4 Hz, 2H, H2C=CHCH2). 13C NMR (CDCl3, 50 MHz) delta 166.9 (CO2CH3); 132.4 (H2C=CHCH2); 119.4 (H2C=CHCH2); 65.7 (C(CO2CH3)3); 53.1 (CO2CH3); 37.6 (H2C=CHCH2). IR (neat), cm-1: 2900; 1740; 1460; 1370; 1230. Anal. for C10H14O6 (M=230.22 g mol-1): calcd (%) : C=52.17; H=6.13. found (%) : C=52.06; H=6.32.

The synthetic route of 40637-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Agarwal, Jyoti; Commandeur, Claude; Malacria, Max; Thorimbert, Serge; Tetrahedron; vol. 69; 45; (2013); p. 9398 – 9405;,
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3549-23-3, name is Methyl 2-(4-(tert-butyl)phenyl)acetate, 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. Recommanded Product: Methyl 2-(4-(tert-butyl)phenyl)acetate

The appropriate aryl-ester 18a-e (1 eq), was added of EtOH (2.22 ml*mmol/eq) followed by hydrazine monohydrate (3 eq). The solution was refluxed overnight, then cooled to room temperature. The precipitate obtained was filtered and washed with cold EtOH and n-hexane to give the pure product. Synthesised as described above for hydrazides 19a-e. Obtained as a yellow oil in 88percent yield as a white solid.1H-NMR (DMSO-d6), delta: 1.26 (s, 9H), 3.30 (s, 2H), 4.13 (bs, 2H), 7.18 (d, J = 8.2 Hz, 2H), 7.30 (d, J = 8.2 Hz, 2H), 9.18 (bs, 1H). 13C-NMR (DMSO-d6): delta: 31.1, 39.9, 34.1, 124.7, 124.8, 133.2, 148.6, 169.6.

The synthetic route of 3549-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Giancotti, Gilda; Cancellieri, Michela; Balboni, Andrea; Giustiniano, Mariateresa; Novellino, Ettore; Delang, Leen; Neyts, Johan; Leyssen, Pieter; Brancale, Andrea; Bassetto, Marcella; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 56 – 68;,
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583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate, 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. category: esters-buliding-blocks

General procedure: To a solution of 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl iodide (0.22 mL, 1.0 mmol), ethyl benzoate (0.16 mL, 1.1 mmol) in Et2O (3 mL) was added at -80C methyllithium (1.5 M in Et2O with lithium bromide; 0.73 mL, 1.1 mmol) and stirring was continued for 30 min at the same temperature where diethyl-aluminium chloride (1 M in n-hexane; 1.1 mL, 1.1 mmol) was gradually added and further stirring for 15 min at -80 C. In a separate flask, lithium bromide (0.12 g, 1.4 mmol), triethyl phosphonoacetate (0.26 mL, 1.3 mmol), and THF (1 mL) was mixed at 0 C where triethylamine (0.19 mL, 1.4 mmol) was added and the solution was stirred for 10 min at room temperature. This mixture was slowly introduced to an aluminium acetal solution prepared above with the aid of cannula and the whole mixture was further stirred for 1 h at room temperature. To this solution were successively added Et2O (3 mL), NaF (0.185 g, 4.4 mmol) and H2O (59 mg, 3.3 mmol), which was stirred for 0.5 h at room temperature. Filtration with a pad of silica gel and concentration furnished a crude mixture which was purified by silica gel column chromatography (n-hexane:CH2Cl2=6:1) to afford 0.484 g (0.979 mmol, 98% yield, E_Z=>99:1) of the title compound 5ca as a colourless oil.

The synthetic route of 583-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yamazaki, Takashi; Mano, Noriko; Hikage, Reo; Kaneko, Tsutomu; Kawasaki-Takasuka, Tomoko; Yamada, Shigeyuki; Tetrahedron; vol. 71; 42; (2015); p. 8059 – 8066;,
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Reference of 6836-21-1, 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. 6836-21-1, name is Ethyl 2-(7-methoxynaphthalen-1-yl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(2-methoxy naphthalen-8-yl)acetate (2.0 g, 8.1 mmol)was dissolved in ethanol (40 mL, 20 vol) and cooled to -78 to-74 C, ammonia gas was purged to reaction mass for 30 minat -78 to -74 C, after purging slowly allowed to 25-30 C and stir for 2 h. The reaction mass stored for 48 h at 25-30 C,then mass was concentrated completely under reduced pressureto obtained crude material which was triturated in toluene (20mL, 10 vol) for 1 h and filtered the solid, then washed withtoluene (10 mL, 5 vol) suck dried the compound to get paleyellow coloured solid (1. 5 g, 87.6 % yield).IR (KBr, numax, cm-1): 3395, 3203, 2939, 2831, 1643, 1401,1259, 1203, 1024, 827 ; 1H NMR (400 MHz, DMSO-d6): delta7.84 (d, J = 8.8 Hz, 1H), 7.73 (d, J = 7.0 Hz, 1H), 7.61 (brs,1H), 7.4 (t, J = 6.8 Hz, 2H), 7.28 (t, J = 7.2 Hz, 1H), 7.19 (dd,J1 = 2.0 Hz, J2 = 9.2 Hz, 1H), 7.02 (brs, 1H), 3.87 (s, 3H), 3.81(s, 2H); 13C NMR (100Hz, DMSO-d6): delta 172.14, 157.22,133.14, 131.67, 129.87, 128.65, 128.20, 126.62, 123.01,117.58, 103.37, 55.11; EI-MS m/z (%): 216 (M + 1, 84), 199(27), 171 (100).

The synthetic route of Ethyl 2-(7-methoxynaphthalen-1-yl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gurunadham; Raju, R. Madhusudhan; Venkateswarlu; Asian Journal of Chemistry; vol. 28; 6; (2016); p. 1367 – 1370;,
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