Category: esters-buliding-blocks

Application of 52727-57-8, The chemical industry reduces the impact on the environment during synthesis 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, I believe this compound will play a more active role in future production and life.

Intermediate 108To a solution of methyl 2-amino-5-bromobenzoate (7.38 g, 32.0 mmol) and pyridine (6.3 mL, 81.5 mmol) in 100 mL of anhydrous CH2CL2, was added slowly methane sulfonylchloride (6.5 mL, 79.9 mmol). After stirring overnight, reaction mixture was quenched with 100 mL of IN HC1 (aq). Aqueous mixture was extracted with ethyl acetate (3×120 mL) and combined organic layers were washed 200 mL brine. Organics were dried (MgS04), filtered, and concentrated under reduced pressure to yield intermediate 108 as an off white solid. Silica gel column chromatography (0-30% Ethyl Acetate in Hexanes), yielded intermediate C-C (9.35 g, 95 %) as a white off- white solid.1 H-NMR (CDC13, 300 MHz): delta 10.4 (s, IH), 8.22 (s, IH), 7.63 (s, 2H), 3.96 (s, 3H), 3.05 (s, 3H) LCMS m/z [M+H]+ C9Hi0BrNO4S requires: 307.95. Found 308.06

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-amino-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); 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. 106-65-0, name is Dimethyl succinate, A new synthetic method of this compound is introduced below., Safety of Dimethyl succinate

Potassium (3.10 g, 0.08 mol) andt-BuOH (110 ml) were stirred at 60 C for 3 h under nitrogen until the potassium disappeared. t-BuOH was evaporated under reduced pressure to obtain the white solid (t-BuOK). Then (3,4-dimethoxyphenyl)(phenyl)methanone (5) (15.00 g, 0.06 mol), dimethyl succinate (11.50 g, 0.07 mol), and toluene (100 ml) were added and stirred at 110 C for 34 h. After completion of the reaction, water (100 ml) was added, and the aqueous phase was extracted with toluene (3¡Á50 ml). The combined organic phases were dried over anhydrous Na2SO4, concentrated under reduced pressure, and product 6 was purified by recrystallization from n-hexane-EtOAc, 4:1. Yield 18.86 g (85 %), yellow solid,mp 211-212 C. 1H NMR spectrum, delta, ppm (J, Hz): 3.48(3H, d, J = 2.4, OCH3); 3.59 (2H, s, CH2); 3.78 (3H, s,OCH3); 3.89 (3H, s, OCH3); 6.68-6.73 (2H, m, H Ar); 6.83-6.87 (1H, m, H Ar); 7.10-7.14 (2H, m, H Ar); 7.26-7.29 (3H,m, H Ar). 13C NMR spectrum, delta, ppm: 27.4; 38.4; 51.7;55.9; 81.2; 110.9; 112.5; 122.2; 123.4; 127.9; 128.8; 133.8; 141.9; 148.7; 149.3; 152.8; 169.2; 170.2; 177.2. Found, %:C 67.26; H 5.73. C20H20O6. Calculated, %: C 67.41; H 5.66

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:
Article; Zhao, Qian; Yang, Yanhua; Duan, Yingxiang; Tao, Xian; Shen, YingZhong; Chemistry of Heterocyclic Compounds; vol. 54; 9; (2018); p. 840 – 847; Khim. Geterotsikl. Soedin.; vol. 54; 9; (2018); p. 840 – 847,8;,
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Reference of 121-98-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 121-98-2 name is Methyl 4-methoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 192 – 194;,
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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. 685-88-1, name is Diethyl fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Diethyl fluoromalonate

2-fluoromalonic acid diethylester is manufactured from 2-chloromalonic acid diethylester and l,8-diazabicyclo[5,4,0]undec-7-ene- l,37HF neat at 80C, as described in example 2 of US 7,145,046. The raw product is hydrolyzed, in analogy to example 1 of DE-Offenlegungsschrift 4120704, by contacting it with NaOH in water (concentration of NaOH : 30% by weight). Resulting ethanol is removed by distillation, and the resulting solution is contacted withLewatit S 100 in the H-form (i.e. comprising acidic H+). The aqueous solution of fluoromalonic acid is mixed with toluene, and at a reduced pressure(400 mbar), a water/toluene mixture is removed.The resulting fluoromalonic acid then reacted with acetone as described by D. Davidson and S. A. Bernhard in J. Chem. Soc. 70(1948), page 3428, 1. paragraph in chapter “Experimental”. The fluoromalonic acid is suspended in acetic anhydride and concentrated sulfuric acid is added. The amounts of the reagents and starting compounds correspond to those described by Davidson et al.The acetone is added under cooling. After a post-reaction phaseof 2 hours, 5-fluoro-2,2-dimethyl-l,3-dioxane-4,6-dione can be isolated.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; BRAUN, Max Josef; WO2013/79397; (2013); 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, A new synthetic method of this compound is introduced below., Product Details of 685892-23-3

A mixture of methyl 2-bromo-6-chlorobenzoate (750 mg, 3 mmol), (PPh 3) 4 Pd (345 mg, 0.3 mmol) and cyclobutyl zinc bromide (0.5 M in THF, 12 mL) was mixed under N 2 protection. The mixture was stirred under N 2 at 70 C. for 12 h. The mixture was extracted with EtOAc and water. The organic phase was washed with brine, dried over Na 2 SO 4, filtered and concentrated. The residue was purified by flash chromatography (PE: EtOAc = 50: 1) to give the title compound.

The synthetic route of 685892-23-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mrck Sharp and Dohme Corp; Blair T, Lapointe; Peter H, Fuller; Hakan, Gunaydin; Kun, Liu; Daneille F, Molinari; Qinglin, Pu; Mark E, Scott; B Wesely, Trotter; Hongjun, Zhang; (117 pag.)JP2018/531957; (2018); A;,
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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. 820236-81-5, name is Methyl 2-bromo-6-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 820236-81-5

[00500] Methyl 2-bromo-6-fluorobenzoate (38) (11.29 g, 48.5 mmol), cyclopropylboronic acid (6.24 g, 72.7 mmol), K3P04 (30.85 g, 145.4 mmol) and Pd(PPh3)4 (2.80 g, 2.4 mmol) were mixed under argon in a degassed mixture of toluene and water (20: 1, 160 mL). The resulting brown suspension was heated at reflux for 2.5 h, cooled, filtered through Celite, and evaporated. The residue was partitioned between ethyl acetate (150 mL) and brine (150 mL). The layers were separated and organic layer was dried over magnesium sulfate and evaporated. The oily residue was suspended in hexane and the solid was removed by filtration. Evaporation of the filtrate afforded the title compound (9.30 g, 47.9 mmol, 99%) as a light brown oil.

According to the analysis of related databases, 820236-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AFRAXIS, INC.; CAMPBELL, David; DURON, Sergio, G.; WO2013/86451; (2013); A2;,
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Ester – an overview | ScienceDirect Topics

Application of 40546-94-9, 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. 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 3,4-Dihydro-6-methyl-4-phenyl-2H-benzopyran-2-ol (IV) 3,4-Dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one (III, EXAMPLE 1, 100.0 g, 420.2 mmol) is added to toluene (500 mL). The mixture is degassed by purging alternately with vacuum and nitrogen and then cooled to -21. Diisobutylaluminumhydride in toluene solution (DIBAL, 1.5 M, 290 mL, 435 mmol) is then slowly added over 2 hr via add funnel while maintaining the reaction temperature at -20 to -25. The reduction is usually done when the DIBAL add is completed. If the reaction is not done additional DIBAL can be added in increments. When the reaction is done (<1% lactone) ethyl acetate (45 mL) is added at -20 to -25 via add funnel. Very little exotherm is observed. Next, citric acid (23%, 500 mL) is added. The mixture is stirred at 45-50 for 1 hr (or stirred overnight at 20-25), the phases are separated, the organic phase is washed with water (2 x 300 mL). The organic phase is concentrated to 250 mL under reduced pressure. Methanol (500 mL) is added, and the mixture is concentrated to 250 mL. The methanol addition and distillation is repeated to give the title compound in methanol solution. This solution is concentrated to a thick oil which crystallizes on standing to give the title compound (as a mixture of diastereomers), IR (neat) 3410, 3020, 2925, 1605, 1498, 1447, 1205 and 1010 cm-1; MS (m/z, EI) = 240 (parent). Rather then isolating and characterizing the title compound, it is normally taken directly into the next step. HPLC (column = zorbax C-8; mobile phase acetonitrile/water (50/50); flow rate = 1 mL/min; wavelength = 240 nm; note - the absorbance of the lactone (III) at 240 nm is approximately 3.5 times greater than the lactol (IV);. The chemical industry reduces the impact on the environment during synthesis 6-Methyl-4-phenylchroman-2-one. I believe this compound will play a more active role in future production and life. Reference:
Patent; PHARMACIA & UPJOHN COMPANY; EP960109; (2002); B1;,
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Adding a certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 59247-47-1, name: tert-Butyl 4-bromobenzoate

To a 50 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5- yl]methoxy]-2-azabicyclo [2.2.1] heptane li (200 mg, 0.53 mmol, 1.00 equiv.), toluene (5 mL), Pd(OAc)2 (25 mg, 0.11 mmol, 0.20 equiv.), Xantphos (64 mg, 0.11 mmol, 0.20 equiv), Cs2CO3 (518 mg, 1.59 mmol, 3.00 equiv.), and tert-butyl 4-bromo-2-fluorobenzoate (134 mg, 0.49 mmol, 1.10 equiv.). The resulting mixture was heated at 90¡ãC overnight and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1/3) to give tert-butyl 4-[(1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1] heptan-2-yl]-2-fluorobenzoate 2a (176 mg, 58percent) as a yellow solid

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, tert-Butyl 4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
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Reference of 1186-73-8, The chemical industry reduces the impact on the environment during synthesis 1186-73-8, name is Trimethyl methanetricarboxylate, I believe this compound will play a more active role in future production and life.

Step 5; methyl 9-chloro-l-(2,4-dimethoxybenzyl)-4-hydroxy-2-oxo-l,2,5,6- tetrahydrobenzo [2,3] oxepino [4,5-b] pyridine-3-carboxylate A solution of N-(8-chloro-3 ,4-dihydrobenzo [b] oxepin-5 (2H)-ylidene)- 1 -(2,4- dimethoxyphenyl)methanamine (4.4 g crude) and trimethyl methanetricarboxylate (4.9 g, 25.6 mmol) in Pl^O (13 mL) was heated at 230 C for 15 min. The reaction mixture was cooled to room temperature, and purified on silica gel using EtO Ac/Hex (0-60% gradient) to afford the product (2.6 g, 43%) as a yellow foam. XH NMR (500 MHz, CHCl3-i/) delta ppm 2.06 – 2.17 (m, 1 H) 3.18 (dd, J=15.09, 3.90 Hz, 1 H) 3.63 – 3.68 (m, 3 H) 3.75 – 3.79 (m, 3 H) 3.99 (s, 3 H) 4.37 (dd, J=9.81, 6.34 Hz, 1 H) 4.41 – 4.50 (m, 1 H) 4.93 – 5.04 (m, 1 H) 5.15 (d, J=15.76 Hz, 1 H) 6.32 – 6.44 (m, 2 H) 6.94 (d, J=8.35 Hz, 1 H) 7.06 – 7.12 (m, 2 H) 7.17 (s, 1 H) 13.80 (s, 1 H). LC-MS: 470.1 [M-H]”, RT 1.45 min.

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, Trimethyl methanetricarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Synthetic Route of 685-88-1,Some common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, molecular formula is C7H11FO4, 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.

6-Fluoroimidazo[1 ,2-a]pyridine-3-carboximidamide (Preparation 1 b, 2.0 g, 8.39 mmol,) was added portionwise to a stirred solution of sodium (0.46 g, 20.21 mmol) in methanol (35 mL) at 0 C. Diethyl 2-fluoromalonate (2.65 mL, 16.8 mmol) was then added and the reaction mixture was stirred from 0 C to room temperature overnight. The solvent was evaporated to dryness and the resulting crude was dissolved in water (90 mL). After stirring for 30 min, a 2N solution of hydrochloric acid was added until acid pH. The solid formed was filtered and dried to yield the title compound (0.95 g, 43%) as a brown solid that was used in the next synthetic step without further purification. LRMS (m/z): 265 (M+1 )+ 1H NMR delta (300 MHz, DMSO-d6): 7.6 (s, 1 H), 7.8 (s, 1 H), 8.7 (s, 1 H), 10.1 (s, 1 H), 12.6 (bs, 1 H).

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

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); A1;,
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