Tag: M.W=100-200

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. 53088-68-9, name is Methyl (3-Chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Formula: C9H9ClO2

REFERENCE EXAMPLE 30 Methyl (RS)-a-bromo-(3-chlorophenyl)acetate A mixture of Reference Example 29 (5.0 g), N-bromosuccinimide (5.3 g) and azobisisobutyronitrile (0.38 g) in dry chloroform (50 ml) was heated at reflux for 6 hours. The reaction mixture was washed four times with water (50 ml) and the organic phase dried over magnesium sulphate and evaporated. The residual oil was purified by flash chromatography on silica eluding with a mixture of ethyl acetate and pentane (5:95, v/v). Fractions homogenous in the required product were combined and evaporated to give the title compound (4.3 g) as an oil.

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; Rhone-Poulenc Rorer Limited; US6048893; (2000); A;; ; Patent; Rhone-Poulenc Rorer Limited; US6124343; (2000); A;,
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Adding a certain compound to certain chemical reactions, such as: 94-46-2, name is Isoamyl Benzoate, 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 94-46-2, Safety of Isoamyl Benzoate

Trifluoromethylthio silver (0.5 mmol), 2,6-lutidine (0.1 mmol) and ammonium persulfate (1.0 mmol) were added to the reaction flask, and after evacuating the argon three times, isoamyl benzoate 1.0 mmol) and acetonitrile (5 mL). The reaction flask was placed in an oil bath at 90 C start heating and stirring 2h removed, to be cooled to room temperature. Using trifluoromethylbenzene as an internal standard substance, it was confirmed by 19F-NMR that 3-methyl-3-trifluoromethylthiobutyl benzoate was formed (a yield of 63%). The reaction mixture was filtered and the filtrate was evaporated to remove the solvent by a rotary evaporator. The residue was separated by column chromatography and concentrated under reduced pressure to give a colorless oil (75 mg, yield 51%).

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; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Chen Qingyun; Liu Chao; Wu Hao; Xiao Zhiwei; (15 pag.)CN104557358; (2017); B;,
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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. 73792-12-8, name is Ethyl 4-amino-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 73792-12-8

Step 1 : Ethyl 3-fluoro-4-hydrazinylbenzoate hydrochloride: To a stirred and cooled (-20C) solution of ethyl 4-amino-3-fluorobenzoate (18 g, 98.809 mmol) in cone. HC1 (200 mL) was added aqueous solution of NaN02 (7.5 g, 108.69 mmol). This mixture was added very slowly to a precooled (-10 C) mixture of and tin chloride (100 g, 444.7 mmol) in cone. HC1 (80 mL) and stirred at the same temperature for 30 min. The precipitate obtained was filtered and washed with diethyl ether (2 x 100 mL) to obtain 19.6 g of the title compound as white solid. 1H NMR (300 MHz, DMSO-i) delta 1.30 (t, J = 7.2 Hz, 3H), 4.27 (q, J = 6.9 Hz, 2H), 7.19 (t, J = 8.1 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.78 (d, J = 8.4 Hz, 1H), 8.94 (br s, 1H), 10.50 (br s, 2H); APCI-MS (m/z) 199 (M+H)+.

According to the analysis of related databases, 73792-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; CHAUDHARI, Sachin Sundarlal; THOMAS, Abraham; PARDESHI, Shailesh Ramesh; DESHMUKH, Vishal Govindrao; WADEKAR, Prashant Dilip; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; WO2015/87234; (2015); A1;,
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Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, 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.

Lithium diisopropylamide was prepared by addition of n-butyllithium (2.5 M in hexanes, 11.7 mL, 58.8 mmol) to diisopropylamine (9.7 mL, 70.6 mmol) in dry tetrahydrofuran (100 mL) at -78 C. Stirring was continued for 15 min at -78 C before methyl 4-methoxybutanoate (6.84 g, 51.8 mmol) was added to the reaction mixture. Stirring was continued for 20 min at -78C and benzaldehyde (5g, 47.1 mmol) in tetrahydrofuran (20 mL) was added, and the reaction mixture allowed to warm slowly to room temperature. Stirring was continued for 2 hours, water (50 mL) was added under stirring and the mixture was extracted with ether (3 x 50 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated under reduced pressure to afford methyl 2-(hydroxy(phenyl)methyl)-4-methoxybutanoate (10.7 g, 44.9 mmol) in 95% yield. LCMS (ESI+): 261.1 (M+Na).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-methoxybutanoate, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COTE, Alexandre; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-christophe; VASWANI, Rishi, G.; (274 pag.)WO2016/172496; (2016); 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. 111-79-5, name is Methyl non-2-enoate, A new synthetic method of this compound is introduced below., Recommanded Product: 111-79-5

PREPARATION 2 4-Nitro-beta-hexyl-1H-imidazole-1-propanoic acid methyl ester The title intermediate was prepared by combining 5.0 grams of 4-nitroimidazole, 8.26 g of methyl 2-nonenate, 4.08 g of sodium bicarbonate, and 200 ml of dimethylformamide and heating the mixture at 80 C. for 18 hours. After cooling, the mixture was poured into water and extracted into ethyl acetate. The organic layer was concentrated in vacuo and the residue purified by HPLC over a silica column eluding with ethyl acetate. The appropriate fractions were combined and concentrated in vacuo to provide 2.2 g of the desired titled intermediate. Analysis for C13 H21 N3 O4: Calc.: C, 55.11; H, 7.47; N, 14.83; Found: C, 55.37; H, 7.37; N, 14.58.

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; Eli Lilly and Company; US5073566; (1991); A;,
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Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, 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. COA of Formula: C9H8O4

General procedure: (i) [Ir(coe)2Cl]2 (0.9 mg, 0.1mol %) and aryl acetates 1 (1 mmol) were added to a flame-dried, nitrogen-purged septum-capped vial. The mixture was dissolved with THF (0.3 mL, 3.3 M), and diethylsilane (0.26 mL, 2 mmol) was added to the mixture. The septum on the vial was replaced by a screw cap with a Teflon liner under a N2 atmosphere [note: diethylsilane (bp 56 C and density 0.686 g/mL) is volatile]. The reaction mixture was stirred for 3-12 h at 60 C. Volatiles were removed in vacuo to afford silyl acetals, which were directly used for subsequent reactions without further purification. (ii) [Rh(nbd)Cl]2 (1.8 mg, 0.4 mol %), tris(4-methoxyphenyl)phosphine (8.4 mg, 2.4 mol %), norbornene (188 mg, 2 mmol), and THF (1 mL, 1M) were added to the crude silyl acetals (1 mmol). The septum on the vial was replaced by a screw cap with a Teflon liner, and the mixture was stirred at 120 C for 15 min. The reaction progress was monitored by GC/MS spectrometry. The resulting benzodioxasilines 3 were directly used for a subsequent reaction without further purification. For hindered substrates 3o-r, the resulting benzodioxasilines 3 were purified for the subsequent reactions; volatiles were removed in vacuo, and the resulting mixture was dissolved with pentane, filtered through a pad of Celite, and concentrated in vacuo. The crude product was purified by MPLC (hexanes/EtOAc=80:1, 5mL/min, retention time 5-15 min). (iii) The crude benzodioxasilines 3 (1 mmol, THF, 1M) were diluted with diethyl ether (3 mL, 0.33 M) and cooled to -78 C. MeLi (3 mmol, 1.6 M in Et2O) were added into the reaction mixture at -78 C and stirred for 1 min. (iv) Trifluoromethanesulfonyl anhydride (1.2 mmol, 0.2 mL) was added into the reaction mixture. The reaction mixture was warmed to rt and stirred for 30 min. The reaction mixture was cooled to 0 C and saturated aqueous ammonium chloride solution was added. The mixture was extracted with diethyl ether three times. The combined organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. Volatiles were removed in vacuo, and the crude mixture was purified by MPLC to afford arylsilyl triflates 5 (hexanes/EtOAc=40:1, 5mL/min, retention time 6-20 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.

Reference:
Article; Asgari, Parham; Dakarapu, Udaya Sree; Nguyen, Hiep H.; Jeon, Junha; Tetrahedron; vol. 73; 29; (2017); p. 4052 – 4061;,
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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. 14659-60-0, name is Methyl 4-fluoro-2,6-dimethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H11FO2

4-Amino-2,6-dimethyl benzoic acid (200 mg, 1.1 mmol) and NOBF4 (196 mg, 1.7 mmol) were heated in 1,2-dichlorobenzene at 100 C for 30 min. The solution was cooled and diluted with MeOH and water. A few pellets (2-3) of KOH were added, and the solution was heated at reflux for 16 h. The solution was concentrated. The residue was partitioned between Et2O and 1 N NaOH. The aqueous layer was extracted with Et2O. The aqueous layer was cooled to 0 C and acidified with conc. HCl (pH = 1-2). The aqueous layer was extracted with CH2Cl2. The organic layers were dried (Na2SO4). Filtration and concentration gave 58 mg (31 %) of the acid as a tan solid.

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 14659-60-0.

Reference:
Patent; SCHERING CORPORATION; EP1175401; (2005); 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 13031-39-5 as follows. HPLC of Formula: C8H7ClO2

3-chlorophenyl acetate (starting material 2) was mixed with aluminium chloride (3 eq). The mixture was heated at 200 C. for 1 hour. The reaction medium was cooled to room temperature then poured in ice. The aqueous phase was extracted with methylene chloride which was dried on magnesium sulfate then vacuum evaporated. Purification was by silica gel chromatography (elution: cyclohexane/ethyl acetate 95:5). 1 H NMR CDCl3 deltappm: 3.41 (s, 3 H), 6.81 (dd, J=8.82 Hz, J=1.47 Hz, 1H), 6.91 (d, J=1.47 Hz, 1H), 7.60 (d, 8.82 Hz, 1 H), 12.33 (s, 1H) Reference: Chen et al, J Chem Soc, 1958, 146-148.

According to the analysis of related databases, 13031-39-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENFIT; US2005/171149; (2005); A1;,
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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. 2459-25-8, name is Methyl 2-naphthoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C12H10O2

General procedure: To a solution of methyl 4-methylbenzoate (6.0 g, 40mmol, 1.0 equiv) in toluene (200 mL) was added TMSCF3 (11.3 g, 80 mmol, 2.0 equiv) at room temperatureunder Ar. The reaction mixture was cooled to -78 oC, TBAF (4 mL, 1.0 M in THF, 0.1 equiv) was then added.After stirring for 0.5 h at -78 oC, the reaction mixture was allowed to warm to room temperature and stirred forfurther 12 h. Hydrochloric acid (30 mL, 2.0 M, 1.5 equiv) was then added and the resulting mixture stirred forfurther 2 h. The resulting suspension was quenched with saturated aqueous NaHCO3 and extracted with ethylacetate. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue waspurified by flash column chromatography to give ketone 10a.

The synthetic route of 2459-25-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Xing; Cheng, Ran; Xiao, Yu-Lan; Wan, Xiao-Long; Zhang, Xingang; Chem; vol. 5; 11; (2019); p. 2987 – 2999;,
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Synthetic Route of 1268830-91-6, The chemical industry reduces the impact on the environment during synthesis 1268830-91-6, name is Methyl 3-amino-6-fluoro-2-methoxybenzoate, I believe this compound will play a more active role in future production and life.

A 250 mL round bottom flask was charged with a solution of methyl 3- amino-6-fluoro-2-methoxybenzoate (3.656 g, 18.36 mmol) in methylene chloride (100 mL). To this reaction mixture was added a solution of 4-dimethylaminopyridine (113 mg, 0.925 mmol), pyridine (7.45 mL, 92.1 mmol) and propane- 1-sulfonyl chloride (8.25 mL, 73.6 mmol) in methylene chloride (10 mL) over a course of five minutes. The reaction mixture was stirred at room temperature for 14 hours. After removing the organic solvent under reduced pressure, 100 mL saturated aqueous sodium bicarbonate was added followed by stirring for 10 minutes. The aqueous mixture was extracted with 200 mL ethyl acetate (2x). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified using flash chromatography, eluting with 0-30% ethyl acetate/heptanes to give methyl 6-fluoro-2-methoxy-3-(propylsulfonamido)benzoate as an oil (4.914 g, 85%). 1H NMR (400 MHz, DMSOd6) delta = 9.27 (s, IH), 7.48 (dd, J=9.1, 6.1, IH), 7.09 (t, J=9.0, IH), 3.89 (s, 3H), 3.85 – 3.74 (m, 3H), 3.29 (s, 15H).

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-amino-6-fluoro-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; ALIAGAS, Ignacio; GRADL, Stefan; GUNZNER, Janet; MATHIEU, Simon; RUDOLPH, Joachim; WEN, Zhaoyang; WENGLOWSKY, Steven Mark; WO2011/25947; (2011); A1;,
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