Tag: M.W=200-300

Reference of 583-02-8, 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. 583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2,2,6,6-tetramethylpiperidine (TMPH, 1.5equiv) in THF (2mL/mmol of ester), a solution of n-butyllithium (1.45M in hexane, 1.5equiv) was added at -30C over 30min. After cooling at -78C, tris(isopropyl)borate (2.0equiv) was added over 20min. Ethyl benzoate or 4-(trifluoromethyl)benzoate or ethyl isonicotinate (1.0equiv) was added via syringe to the reaction mixture over 10min and the mixture was stirred at -78C for 3.5h. After warming to -30C, glacial acetic acid (1.5equiv) was added causing the internal temperature rising to -10C. Neopentyl glycol (1.5equiv) was added and the mixture was stirred at room temperature for 2h. Dichloromethane (20mL/mmol of ester) was then added. The organic phase was successively washed three times with satd aqueous NH4Cl, with satd aqueous NaHCO3 and with water, dried over MgSO4 and evaporated to give the desired compounds.

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, Ethyl 4-(trifluoromethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fresneau, Nathalie; Cailly, Thomas; Fabis, Frederic; Bouillon, Jean-Philippe; Tetrahedron; vol. 69; 26; (2013); p. 5393 – 5400;,
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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. 76008-73-6, name is Ethyl 5-bromo-2-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H8BrClO2

Under a nitrogen atmosphere, a 50 mL round bottom flask is charged with bis(pinacolato)diborane (1.16 g, 4.55 mmol), potassium acetate (1.11 g, 11.4 mmol) and 5-bromo-2- chloro-benzoic acid ethyl ester (1 g, 3.79 mmol). After bubbling nitrogen through the mixture for 5 minutes, dichloro[l,r-bis(diphenylphosphino)ferrocene]palladium DCM adduct [PdCl2(dppf), 93 mg, 0.11 mmol] is added. The resulting mixture is heated to 60C for 2 hours, cooled to room temperature and poured into EtOAc (50 mL). This mixture is washed with water, with brine, dried over sodium sulfate, filtered and concentrated to give 2-chloro-5-(4A5,5-tetramethyl-[l . 3,2″|dioxaborolan-2-yl)- benzoic acid ethyl ester [LCMS: Rtau = 5.1 minutes, MS: 311 (M+H)] and the dimerized side product, 4,3′-Dichloro-biphenyl-3,4′-dicarboxylic acid diethyl ester in 2:1 ratio (0.65 g total). The crude mixture is used for a next step without further purification.

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 76008-73-6.

Reference:
Patent; SANOFI-AVENTIS U.S. LLC; HARRIS, Keith John; WO2008/39882; (2008); A1;,
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Electric Literature of 185312-82-7, 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 185312-82-7 as follows.

In the same manner as in Preparation Example 80-1, the objective compound (908 mg) was obtained as a colorless oil from methyl 4-bromo-2-chlorobenzoate (1 g). 1H-NMR(CDCl3): 3.91(3H, s), 4.19(2H, s), 7.15(1H, dd, J=8, 1 Hz), 7.23-7.43(6H, m), 7.75(1H, d, J=8 Hz)

According to the analysis of related databases, 185312-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6348474; (2002); B1;,
Ester – Wikipedia,
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Application of 40546-94-9,Some common heterocyclic compound, 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, molecular formula is C16H14O2, 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.

Example 17 [0091] A solution of 0.50 g of 6-methyl-4-phenyl-2-chromanone, 2.65 g of N-fluorobenzenesulfonimide, 22 ml of THF and 6.5 ml of toluene, was cooled to -100 C., and 7.34 ml of a 1.0M THF solution of potassium hexamethyldisilazide was added. After raising the temperature to room temperature, an aqueous citric acid solution was added to terminate the reaction, followed by extraction with ethyl acetate, and the solvent was removed. 0.87 g of the obtained product was quantitatively analyzed by 19F NMR, whereby it was confirmed that 3,3-difluoro-6-methyl-4-phenyl-2-chromanone was formed in a yield of 25%. No formation of a monofluoro product was detected. The structural characteristics of the 3,3-difluoro-6-methyl-4-phenyl-2-chromanone are as follows. 19F-NMR (deuterated acetone): -96.5 (bs).

The synthetic route of 40546-94-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Glass Company, Limited; ISHIBASHI, Yuichiro; Matsumura, Yasushi; US2015/175632; (2015); A1;,
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Electric Literature of 59247-47-1, A common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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.

General procedure: Under nitrogen atmosphere, a mixture of alcohol 1a (28.6 mg, 0.10 mmol, 1.0 equiv), 4-bromoanisole (37.4 mg, 0.20 mmol, 2.0 equiv), [C12H8NH2PdCl]2 (1.5 mg, 2.5 mol%), L10 (13.6 mg, 15 mol%) and NaH (7.2 mg, 0.30 mmol, 3.0 equiv) in anhydrous toluene (2.0 mL), were heated at 80C for 12 h. After being cooled to room temperature, the solvent was removed and the residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate = 30:1) to afford the desired product 2a (38.0 mg, 97%, 96% ee).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Deng, Ruixian; Xi, Junwei; Li, Qigang; Gu, Zhenhua; Chem; vol. 5; 7; (2019); p. 1834 – 1846;,
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Application of 2905-67-1, 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. 2905-67-1, name is Methyl 3,5-dichlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 25 g of 3,5-dichlorobenzoic acid methyl and 22.5 g of trifluoromethyltrimethylsilane in 300 g of dimethoxyethane, 0.37 g of cesium fluoride was added with ice-cooling and the mixture was warmed to room temperature and stirred for 4 hours. After disappearance of the raw material was confirmed, 200 g of water was put into the reaction solution to extract with 200 g of ethyl acetate. After the organic layer was dehydrated and dried with saturated saline followed by anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 35.5 g of 1-(3,5-dichlorophenyl)-2,2,2-trifluoro-1-trimethylsilyloxy-1-methoxyethane as yellow liquid matter.

The chemical industry reduces the impact on the environment during synthesis Methyl 3,5-dichlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nissan Chemical Industries, Ltd.; EP1975149; (2008); A1;,
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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. 39149-80-9, name is tert-Butyl 2-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 2-bromopropanoate

CS2CO3 (622mg, l.9lmmol) was added to a stirred mixture of tert- butyl 3-(5,6- dimethoxythieno[3,2-b]pyridin-2-yl)-3-oxopropanoate (322mg, 0.954mmol) in DMF (3mL) at 25C. A mixture of fer/-butyl 2-bromopropanoate (2l0mg, l.OOmmol) in DMF (lmL) was added dropwise to the reaction mixture. The reaction mixture was stirred at RT for 5 hours. Additional /er/-butyl 2-bromopropanoate (63mg, 0.030mmol) was added, and the reaction mixture was stirred for 1 hour. Additional /er/-butyl 2-bromopropanoate (63mg, 0.030mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was diluted with isopropyl acetate (75mL) and sodium citrate (10% w/v in H20, 40mL). The layers were separated, and the aqueous layer was extracted with additional isopropyl acetate (40mL). The organic layers were combined, washed with brine, dried over anhydrous Na^SCri. filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting EtOAC in Hex) to afford di-/er/-butyl 2-(5,6-dimethoxythieno[3,2-b]pyridine-2- carbonyl)-3-methylsuccinate. LCMS (C23H32NO7S) (ES, m/z): 466 [M+H]+.

According to the analysis of related databases, 39149-80-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CASH, Brandon, D.; CUMMING, Jared, N.; DEMONG, Duane, E.; HAIDLE, Andrew, M.; JEWELL, James, P.; LARSEN, Matthew, A.; LU, Min; OTTE, Ryan, D.; TAOKA, Brandon, M.; TROTTER, Benjamin Wesley; TRUONG, Quang, T.; (97 pag.)WO2019/195063; (2019); A1;,
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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 40876-98-0 as follows. Computed Properties of C8H11NaO5

Step 1: 6-hydroxypyrimidine-4-carboxylic acid; 63.5 g (287 mmol) sodium diethyl-oxalacetate and 30.2 g (287 mmol) formamidine acetate were added to 24.1 g (0.597 mol) NaOH in 3.6 L water. The mixture was stirred overnight at RT. Then activated charcoal was added and the mixture was refluxed for 1 h. It was filtered while hot and after cooling acidified with aqueous HCl. The solution was concentrated to dryness by rotary evaporation. The residue contained the desired product and was used in the next step without any further purification.Yield: 83.0 g

According to the analysis of related databases, 40876-98-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2011/172218; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

General procedure: A mixture of 8a-8j (10 mmol), 15a-15d (11 mmol) and K2CO3 (4.15 g, 30 mmol) in DMF (60 mL) was stirred at room temperature (for 15a-15b) or slightly elevated temperatures (35 C for 15d and 45 C for 15c) until the reaction completed as indicated by TLC analysis (typically within 12h). On cooling (if necessary), the reaction mixture was poured into ice-water (200 mL) and the resulting mixture was extracted with CH2Cl2 (100 mL 3). The combined extracts were washed with 5% brine (100 mL 5), dried (Na2SO4) and evaporated on a rotary evaporator to afford the crude product as a residue, which was purified by column chromatography followed by trituration with EtOAc/n-hexane (if the product was solid) to yield the pure product 9a-9q.

According to the analysis of related databases, 35120-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Wei; Liu, Yuqiang; Xie, Yafei; Shang, Qian; Zhou, Zhixing; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Medicinal Chemistry; vol. 13; 3; (2017); p. 260 – 281;,
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Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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. Application In Synthesis of Methyl 2-(3-bromophenyl)acetate

Sodium hydride (60% in oil) (10.4 g, 436 mmol) was added to tetrahydrofuran (400 ml) under argon and heated with stirring to 50 C. Methyl 2-(3-bromophenyl)acetate (20 g, 87.3 mmol) was added drop wise over 30 minutes and heating continued for 90 minutes. The temperature was lowered to below 40 C. and methyl iodide (13 ml, 209 mmol) was added over 10 minutes. The resulting suspension was stirred at room temperature overnight. Water (300 ml) was carefully added and reaction mixture concentrated. Residue was partitioned between diethyl ether (400 ml) and water. The aqueous layer was extracted with diethyl ether (400 ml), and the combined ethereal extracts were dried over sodium sulfate and concentrated. Crude oil was purified by column chromatography, eluding with a gradient from 0% to 20% ethyl acetate in heptane to give methyl 2-(3-bromophenyl)-2-methylpropanoate (14.96 g, 58 mmol, 67%). 1H NMR (400 MHz, CDCl3): delta ppm 7.47 (t, 1H), 7.37 (dt, 1H), 7.24 (dt, 1H), 7.18 (t, 1H), 3.65 (s, 3H), 1.55 (s, 6H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150529-73-0, its application will become more common.

Reference:
Patent; pfizer Inc; US2010/197591; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics