Category: esters-buliding-blocks

114312-57-1, name is Ethyl 3-fluoro-2-methylbenzoate, 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. HPLC of Formula: C10H11FO2

To a solution of 11 g of ethyl 3-fluoro-2-methylbenzoate in 300 ml of carbon tetrachloride is added 12 g of N-bromosuccinimide and the mixture is refluxed with heating for 12 hours. After cooling, the mixture is washed with water and a saturated saline solution and dried over magnesium sulfate and the solvent is distilled off under reduced pressure to give 13 g of ethyl 3-fluoro-2-bromomethylbenzoate. Mass spectrum m/z: 262, 260(M+).

The synthetic route of 114312-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Pharmaceutical Co., Ltd.; US4889858; (1989); 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. 6836-21-1, name is Ethyl 2-(7-methoxynaphthalen-1-yl)acetate, A new synthetic method of this compound is introduced below., Product Details of 6836-21-1

Reference example 3: The preparation of 7-methoxy-1-naphthaleneacetic acid 40g sodium hydroxide was dissolved in 1000ml water and 1000ml 95% ethanol was added. They were mixed. Then, 50g ethyl (7-methoxy-1-naphthyl)-acetate was added into above-mentioned mixture solution and the mixture solution was stirred for 3 hours at room temperature. The reaction was subsequently stopped and vacuum evaporated to remove ethanol, resulting in brown-red liquid. The liquid was washed with 300mlx2 ethyl acetate prior to adding 30ml 95% ethanol into the aqueous layer. The pH was adjusted to 2 by adding concentrated hydrochloric acid in drops with rapid stirring, resulting in a large amount of light brown solid being precipitated. They were filtered and dried to obtain 32g product with mp of 154-156C. The content measured by HPLC is 98.48%, and the yield is 72%.

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; Tianjin Taipu Pharmaceutical Science & Technology Development Co., Ltd.; EP2474522; (2012); A1;,
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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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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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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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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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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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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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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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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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