Month: May 2021

These common heterocyclic compound, 3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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. Recommanded Product: 3697-68-5

A 100-mL round-bottom flask was charged with ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate (1.91 g, 13.3 mmol, 1.00 equiv), TEA (4.03 g, 39.9 mmol, 3.00 equiv), and DCM (40 mL). Methanesulfonyl chloride (2.27 g, 20.0 mmol, 1.50 equiv) was added at 0 C., and the reaction mixture was stirred for 1 h at rt prior to quenching with saturated NH4Cl (30 mL). The resulting solution was extracted with dichloromethane (2*50 mL), and the organic layers were combined, washed with saturated NaHCO3 (30 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to provide 2.83 g (crude) of ethyl 1-(((methylsulfonyl)oxy)methyl)cyclopropane-1-carboxylate.

The synthetic route of Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; (108 pag.)US2018/134674; (2018); A1;,
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Electric Literature of 1245643-11-1, 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. 1245643-11-1, name is Methyl 3,4-diamino-5-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of a mixture of intermediates 3a and 3b (75/25 evaluated by LC/MS) (195g, 554 mmol) in DMSO (2000 mL) was added vinylbutylether (166 g, 1661. mmol) and tri- ethyl amine (400 mL, 2768 mmol, 0.7g/mL) under N2atmosphere. Pd(OAc)2(12.4g, 55mmol) and DPPP (45.6g, 11 lmmol) were added. The mixture was purged again with N2and heated to 100 C overnight. After cooling down to room temperature, HCl (3M, 1845mL, 5536 mmol) was added portionwise under ice batch and the mixture was stirred for 1 hour. The pH of the mixture was adjusted to 8 with NaHC03. The mixture was filtered. The cake was washed with ethyl acetate (1000 mL), then dissolved in CH2C12(1500 mL*2) and filtered. The filtrate was washed with brine (500 mL), evaporated to give a crude yellow solid (200 g) mainly containing intermediate 8a. This residue was purified by silica gel chromatography (eluent: ethyl acetate= 100%). The desired fractions were collected and the solvent was concentrated to dryness under vacuum to give 100 g (57%>) of intermediate 8a as yellow solid.Alternatively, the previous reaction was also carried out using EtOH as solvent at a temperature of 70C.

The synthetic route of Methyl 3,4-diamino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANGIBAUD, Patrick, Rene; QUEROLLE, Olivier, Alexis, Georges; BERTHELOT, Didier, Jean-Claude; MEYER, Christophe; WILLOT, Matthieu, Philippe, Victor; MEERPOEL, Lieven; JOUSSEAUME, Thierry, Francois, Alain, Jean; (114 pag.)WO2018/178280; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 94994-15-7, name is Methyl 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, 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 94994-15-7, COA of Formula: C11H18O3

(1) Methyl 1-(hydroxymethyl)-4-bicyclo[2.2.2]octanecarboxylate (200 mg) was used to perform the synthesis process according to the method described in Reference Example 63-1-(1) thereby giving methyl 1-formyl-4-bicyclo[2.2.2]octanecarboxylate (182 mg) as a colorless oil.

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 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; TANAKA, Hiroaki; KAWAMURA, Madoka; HAMADA, Makoto; KOBASHI, Yohei; ITO, Yuji; SUZUKI, Kazuaki; BOHNO, Ayako; FUNAYAMA, Kosuke; (510 pag.)EP3666766; (2020); A1;,
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Application of 4897-84-1, These common heterocyclic compound, 4897-84-1, name is Methyl 4-bromobutanoate, 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.

STEP B: methyl 4- (nitrooxy) butanoateMethyl 4-bromobutanoate (6.0 g; 33 mmol) was dissolved in CH3CN (120 mL) and silver nitrate (14.0 g, 82.6 mmol) was added. The reaction was heated at 80¡ãC in the dark for 4 hours. Solvent was evaporated and the crude was dissolved in EtOAc (80 mL) .Precipitate was filtered off and organic phase was washed with water (2 x 100 mL) and brine (1 x 100 mL) , dried over Na2SC>4 and concentrated affording the title compound as an oil. (5.0 g, 93percent)1H-NMR (CDCI3) : 4.54 (2H,t J=6.31); 3.73 (3H,s); 2.48 (2H,tJ=7.15) ; 2.08 (2H,m)

Statistics shows that Methyl 4-bromobutanoate is playing an increasingly important role. we look forward to future research findings about 4897-84-1.

Reference:
Patent; NICOX S.A.; ALMIRANTE, Nicoletta; NICOTRA, Alessia; BORGHI, Valentina; ONGINI, Ennio; WO2011/92065; (2011); A1;,
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Electric Literature of 53518-15-3, 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. 53518-15-3, name is 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

7-Amino-4-trifluoromethylcoumarin 3.71 g (16.2 mmol) was dissolved in dichloromethane (20 mL). After slow addition of the distilled pyridine (20 mL) and p-toluenesulfonyl chloride (6.80 g, 35.7 mmol), the mixture was then stirred for 4 h at room temperature. Then ethyl acetate 150 mL was added, followed by wash of citric acid solution for three times and brine once. The resulting solution was dried with sodium sulfate and evaporated, washed with a small portion of cooled dichloromethane and dried in vacuo to give the compound 2 as white solid. Yield: 5.64 g (91%). Mp 193-194 C. 1H NMR (CDCl3, 400 MHz): delta 7.81 (d, J=8.0 Hz, 2H), 7.57 (d, J=8.8 Hz, 1H), 7.30 (d, J=8.0 Hz, 2H), 7.21 (d, J=2.4 Hz, 1H), 7.08 (dd, J1=2.0 Hz, J2=2.0 Hz, 1H), 6.67 (s, 1H), 2.40 (s, 3H). EI-MS: m/z, calcd 383.34, found 383.02.

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, 7-Amino-4-(trifluoromethyl)-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Jun; Zhang, Chun-Fang; Ming, Ze-Zhong; Hao, Ge-Fei; Yang, Wen-Chao; Yang, Guang-Fu; Tetrahedron; vol. 69; 23; (2013); p. 4743 – 4748;,
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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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 609-12-1

Example 18 A mixture of (2-hydroxy-4-methoxyphenyl){4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}methanone (400 mg), ethyl 2-bromo-3-methylbutanoate (302 mg), potassium carbonate (226 mg) and N,N-dimethylformamide (3 ml) was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:4?1:1, v/v), and concentrated. The residue was dissolved in tetrahydrofuran (6 ml), ethanol (4 ml), water (4 ml) and lithium hydroxide monohydrate (116 mg) were added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was neutralized with dil. hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (1:3?3:1, v/v), concentrated, and crystallized from ethyl acetate-hexane to give 2-(5-methoxy-2-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoyl}phenoxy)-3-methylbutanoic acid (382 mg, yield 77%) as colorless crystals. melting point 87 – 88C. 1H-NMR (300 MHz, CDCl3) delta:1.06 (3 H, d, J=6.9 Hz), 1.14 (3 H, d, J=6.9 Hz), 2.36 – 2.46 (1 H, m), 2.47 (3 H, s), 3.86 (3 H, s), 4.85 (1 H, d, J=3.6 Hz), 5.10 (2 H, s), 6.58 (1 H, dd, J=2.4, 8.7 Hz), 6.65 (1 H, d, J=2.4 Hz), 7.11 (2 H, d, J=8.7 Hz), 7.38 (1 H, d, J=8.7 Hz), 7.42 – 7.47 (3 H, m), 7.87 (2 H, d, J=8.7 Hz), 7.99 – 8.04 (2 H, m).

According to the analysis of related databases, 609-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1911738; (2008); A1;,
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Some common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, molecular formula is C4H5ClF2O2, 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. Product Details of 383-62-0

General procedure: A 25 mL oven-dried Schlenk tube was sequentially added N-methylaniline 1 or aniline 4 (0.2 mmol), Ethyl Bromodifluoroacetate 2a (81.2 mg, 0.4 mmol), DMF (1ml) and H2O (1 mL) was added under air. The reaction mixture was stirred for 6 h at 110. The solution was then diluted with ethyl acetate (20 mL), washed with brine (10 mL), extracted with ethyl acetate (3*5 mL), dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The crude reaction mixture was purified by column chromatography (silica gel, ethyl acetate/petroleum ether) yielded the desired product 3 or 5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 383-62-0, its application will become more common.

Reference:
Article; Xu, Zhuo-Wei; Xu, Wen-Yi; Pei, Xiao-Jun; Tang, Fei; Feng, Yi-Si; Tetrahedron Letters; vol. 60; 18; (2019); p. 1254 – 1258;,
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Adding a certain compound to certain chemical reactions, such as: 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, 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 17100-65-1, HPLC of Formula: C9H9BrO3

A mixture of methyl 2-bromo-4- methoxybenzoate (4) (5.9 g, 23.9 mmol), butyl vinyl ether (15.4 mL, 119.4 mmol), Ph3P (939.0 mg, 3.6 mmol), Et3N (4.3 mL, 31.0 mmol), and Pd(OAc)2 (343.0 mg, 1.8 mmol) in MeCN (45 mL) is stirred under argon at 97 C for 18 h, cooled to room temperature, diluted with H2O (50 mL), and filtered through Celite (H2O rinse). The filtrate is concentrated to dryness at reduced pressure. The residue plus tetrahydrofuran (140 mL) and 10% HCl (140 mL) were stirred for 2 h. After tetrahydrofuran removal at reduced pressure, the residue is extracted with dichloromethane (3 x 70 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (16.7% to 33.3% ethyl acetate/hexane) to give 4.8 g (96%) of 5 as a yellow solid, mp 48-50 C. IR 2962, 1733, 1688, 1258 cm”1; 1HNMR (CDCl3) delta 2.50 (s, 3H, CH3CO), 3.86 (s, 6H, CH3O, CO2CH3), 6.76 (d, J= 2.0 Hz, IH, 3-PhH), 6.93 (dd, J= 7.2, 2.0 Hz, IH, 5-PhH), 7.90 ppm (d, J= 7.2 Hz, IH, 6-PhH).

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 2-bromo-4-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BURNHAM INSTITUTE FOR MEDICAL RESEARCH; MERCOLA, Mark; DAWSON, Marcia, I.; CASHMAN, John; WO2010/33643; (2010); 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. 29823-21-0, name is Ethyl 8-Bromooctanoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 8-Bromooctanoate

1h: Preparation of Compound 8 A 3-neck 300 mL round-bottomed flask equipped with a reflux condenser, magnetic stir bar and a nitrogen inlet was charged with 5 g (1 equivalent) of 4-hydroxybenzonitrile, absolute ethanol 150 mL, and 15.7 mL (1 equivalent) of sodium ethoxide. This mixture was stirred at 25 C. for 15 minutes. Ethyl 8-bromooctanoate (10.5 g, 1 equivalent) was then added dropwise over 10 minutes. The resulting mixture was heated to reflux (75 C.) for 72 hours. The reaction mixture was cooled and the solids filtered off. The solvent was removed on a rotary evaporator. The crude residue was dissolved in methylene chloride (200 mL) and washed with saturated NaHCO3 (2*75 mL), H2O (1*100 mL) and brine (1*100 mL). The crude material was then dissolved in ethanol (125 mL) and water (10 mL). LiOH (5 g) was added and the resulting mixture was heated to reflux (75 C.) for 1 hour then stirred at ambient temperature overnight. The solvent was evaporated and 75 mL of H2O was added. The aqueous solution was acidified to a pH of about 3 with concentrated HCl and the flask cooled to 4 C. An off-white colored solid precipitated. This material was collected by vacuum filtration and dried on the high vacuum overnight to give the crude acid. These solids were further purified by recrystallization from Ethyl acetate/hexanes (95/5) and again with chloroform to give 4.5 g of the product, 8-(4-cyanophenoxy)octanoic acid (41% yield). Melting point: 137-140 C. Molecular Formula: C15H19NO3. Combustion analysis: %C: 68.94 (calc’d), 68.57 (found); %H: 7.33(calc’d), 7.13(found); %N: 5.36 (calc’d), 5.28 (found).

The synthetic route of 29823-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moye-Sherman, Destardi; Gschneidner, David; US2003/199427; (2003); A1;,
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Synthetic Route of 99548-56-8, A common heterocyclic compound, 99548-56-8, name is Methyl 2-bromo-6-methylbenzoate, molecular formula is C9H9BrO2, 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.

7-Bromoisoindolin-l-one was prepared by bromination of methyl 2-bromo-6-methyl benzoate (using N-bromosuccinimide and benzoyl peroxide in refluxing CC14) and treatment of the resulting benzyl bromide with ammonia gas in refluxing ethanol. Further elaboration via the procedure of Example 135 gave the title compound. delta (500 MHz, d6 DMSO): 8.62 (1 H, s), 8.24 (1 H, d, J = 7.3 Hz), 7.96 (2 H, d, J = 8.4 Hz), 7.91-7.85 (2 H, m), 7.71-7.64 (4 H, m), 7.40 (1 H, d, J = 16.5 Hz), 7.25 (2 H, d, J = 16.2 Hz), 7.21 (1 H, d, J = 8.8 Hz), 4.36 (2 H, s).

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; MERCK SHARP & DOHME LIMITED; WO2006/21805; (2006); A1;,
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