Esters-buliding-blocks

Some common heterocyclic compound, 260806-90-4, name is Methyl 3-bromo-2-methoxybenzoate, molecular formula is C9H9BrO3, 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. Computed Properties of C9H9BrO3

Methyl 3-bromo-2-raethoxybenzoate (1.9 g, 7.75 mmol, 1.0 eq) was dissolved in toluene and treated with 4-chloro phenyl boronic acid (1.2 g, 7.75 mmol, 1 eq). The reaction mixture was stirred for 10 minutes, purged with nitrogen for 10 minutes and degassed with vacuum. Tetrakis triphenylphosphine palladium (0.447 g, 0.387 mmol, 0.05 eq) and K2CO3 (1.6 g, 11.62 mmol, 1.5 eq) were then added to the mixture. The mixture was heated to reflux for 12 h at 120C and cooled to ambient temperature. The solvents were evaporated under reduced pressure and the reaction mass was diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous Na?SC^ and concentrated under vacuum. The residue was purified by silica gel (60-120) column chromatography eluting with 5-10 % ethyl acetate/hexane as the eluent to afford the desired product (1.7 g, 80 %). 1H NMR (400 MHz, CDCl3) delta 3.49 (s, 3H), 3.93-3.95 (s, 3H), 7.20-7.25 (t, 1H), 7.39- 7.53 (m, 5H), 7.74-7.78 (t, 1H). MS (ESI): 277.1 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 260806-90-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/152082; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 61500-87-6, A common heterocyclic compound, 61500-87-6, name is Methyl 2-amino-4-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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.

2-Amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester; A mixture of 2-amino-4-trifluoromethyl-benzoic acid methyl ester (51.5 g, 235 mmol), iodine (55.1 g, 217 mmol) and silver sulfate (73.3 g, 234 mmol) in EtOH (1560 mL) was stirred for 1 h at r.t. under nitrogen. The suspension was then filtered and the filtrate diluted with EtOAc and washed once with a 10% aqueous sodium thiosulfate solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (67.5 g, 196 mmol, 83%) as a brown solid, m.p. 101-103 0C, ESI-MS: m/z 346 [M+H]+.

The synthetic route of 61500-87-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/108591; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1187318-53-1,Some common heterocyclic compound, 1187318-53-1, name is 3-Bromo-5-fluoro-2-methyl-benzoic acid methyl ester, molecular formula is C9H8BrFO2, 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.

[0517] To a solution of methyl 3-bromo-5-fluoro-2-methylbenzoate (2.0 g, 8.13 mmol) in CCl4 (20 mL) at rt was added NBS (2.2 g, 12.19 mmol) and AIBN ( 533 mg, 3.25 mmol). The suspension was stirred at 90C for 16 hrs, cooled to rt, and filtered. The filtrate was concentrated under vacuum to afford the crude product, which was purified on silica gel with petroleum ether / EA = 50/1 to afford methyl 3-bromo-2-(bromomethyl)-5- fluorobenzoate (2.5 g yield : 96% ) as a yellow oil.

The synthetic route of 1187318-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTHERYX, INC.; CHAN, Kyle, W.H.; FUNG, Leah; SULLIVAN, Robert; ERDMAN, Paul, E.; MERCURIO, Frank; (225 pag.)WO2017/201069; (2017); 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. 76783-59-0, name is Ethyl 3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

General procedure: A typical procedure is as follows. Magnesium turnings (0.36 g, 15 mmol) for Grignard reagent with no pre-treatment were placed in a 100 mL four-necked flask and were heated to dry. Carbon dioxide was introduced to the flask and a balloon filled with carbon dioxide was attached to the flask. Chlorotrimethylsilane (3.17 mL, 25 mmol) in dry DMF (30 mL) was added to the flask and the reaction mixture was stirred for 30 minutes at room temperature. Ethyl benzoate 1a (0.72 mL, 5 mmol) was added dropwise by means of a syringe and the reaction mixture was stirred at room temperature until the starting material disappeared. Then the reaction mixture was carefully poured into 1 M hydrochloric acid solution (100 mL) and the product was extracted with diethyl ether (40 mL) four times. The combined organic layer was washed with 1 M potassium carbonate solution (40 mL) twice and the product was transferred to the water layer. To the combined water layers, 3 M hydrochloric acid (200 mL) was added and the product was extracted with ether (40 mL) four times. The combined ether layer was washed with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the product 2a.

According to the analysis of related databases, 76783-59-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Maekawa, Hirofumi; Okawara, Hikaru; Murakami, Taro; Tetrahedron Letters; vol. 58; 3; (2017); p. 206 – 209;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 57486-69-8, These common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, 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.

Methyl 2-bromophenylacetate (3.8 g) in tetrahydrofuran (50 mL) cool to -78 C,1.6 mol / L lithium hexamethyldisilazide(13.3 mL, 21 mmol) was added dropwise and the mixture was stirred for 1 hour. Subsequently, methyl iodide was added, the temperature was raised to room temperature, and the mixture was stirred for 3 hours. Saturated ammonium chloride aqueous solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, After filtration, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography,The target compound was obtained (3.0 g, 75%).

Statistics shows that Methyl 2-(2-bromophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 57486-69-8.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; SUMIYOSHI, TAKAAKI; TAKAHASHI, YOKO; URUNO, YOSHIHARU; TAKAI, KENTARO; SUWA, ATSUSHI; MURATA, YASUKO; (58 pag.)JP2015/83543; (2015); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 18014-00-1, These common heterocyclic compound, 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, 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.

210 mg of 4-chlorothiophene boric acid,151 mg of dimethyl 2,5-dibromobenzene-1,4-dicarboxylate,116mg PdCl2(PPh3)2, 434.7mg saturated K2CO3 aqueous solution was placed in a two-port bottle,Add 12 mL of tetrahydrofuran,The mixture was heated and stirred under reflux for 9 hours under argon.After cooling to room temperature, it was extracted with 30 mL of ethyl acetate.The combined organic layers were washed with saturated brine andNa2SO4 is dry.The solution was then filtered and the solvent removed to give a crude material which was crystallised from ethanol.The product was obtained as a yellow solid.

Statistics shows that Dimethyl 2,5-dibromoterephthalate is playing an increasingly important role. we look forward to future research findings about 18014-00-1.

Reference:
Patent; Lanzhou University; Zhang Haoli; Liu Duanwu; Lin Zewei; Xu Zhuguo; Shi Zifa; (13 pag.)CN109678877; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 6942-39-8, 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. 6942-39-8 name is Methyl 2-bromo-5-fluorobenzoate, 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.

b)4′-Chloro-4-fluoro-3′-[[(tricyclo[3.3.1.13’7]dec-l-ylmethyl)amino]carbonyl]-[l,l’-biphenyI]-2-carboxylic acid, methyl ester[4-Chloro-3-[[(tricyclo[3.3.1.13>7]dec-l-ylmethyl)amino]carbonyl]phenyl]-boronic acid(Example 2 (a)) (200 mg), 2-bromo-5-fluoro-benzoic acid, methyl ester (Example 51 (a))(170 mg), tetrahydrofuran (2 mL), a solution of potassium carbonate (166 mg) in water (1mL) and fe(triphenylphosphine)palladium(II) chloride (20 mg) were placed in a 10 mLmicrowave vial. The mixture was heated to 70 C for 1 hour in a microwave thenevaporated. The residue was partitioned between dichloromethane (20 mL) and water (20mL). The layers were separated and the aqueous was extracted with dichloromethane(2×20 mL). The combined organics were dried (MgSCU,), filtered and evaporated.Purification by chromatography (SiOa, 1:4 ethyl acetate :isohexane as eluant) gave the sub- title compound as an oil (79 mg).MS: APCI(+ve) 456/458 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-bromo-5-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/25783; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 223519-11-7, 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. 223519-11-7 name is Methyl 3-amino-5-bromo-4-methylbenzoate, 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.

Methyl 3-amino-5-bromo-4-methylbenzoate (1.15 g, 4.62 mmol), triethylamine (1.28 mL, 9.21 mmol) and dichloromethane (20 mL) were added to a 100 mL two-neck flask, then trifluoroacetic anhydride (0.79 mL, 5.6 mmol) was added dropwise at 0C. The reaction mixture was stirred for 1 h at rt. The mixture was concentrated in vacuo to remove solvent. To the residue was added saturated brine (80 mL) and ethyl acetate (80 mL), and the resulting mixture was partitioned. The organic phase was washed with saturated brine (40 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (1.5 g, 95%).MS (ES-API, pos. ion) m/z: 341.0 [M + 2]t

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-4-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; YANG, Xinye; HUANG, Changwei; MA, Facheng; ZHANG, Ji; WANG, Xiaojun; ZHANG, Yingjun; (162 pag.)WO2017/36404; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 10076-48-9, These common heterocyclic compound, 10076-48-9, name is Methyl 2,2-dimethoxypropanoate, 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.

EXAMPLE 5 Methyl 2,2-dimethoxypropionate (66.9 g, 0.45 mol), hydroquinone (0.1 g), quinoline (74.5 g, 0.58 mol) (dried over potassium hydroxide), and acetyl chloride (48.4 g, 0.62 mol) were combined at 5-10 C. in a Fischer-Porter bottle. Powdered potassium hydroxide (0.45 g, 0.008 mol) was added. The reaction mix formed a thick white slurry. The bottle was sealed, stirred with a magnetic stirrer, and placed in a 122 C. oil bath. After three hours the bottle pressure was 19-22 psig. The reaction mixture was diluted with toluene and the quinoline hydrochloride was removed by filtration. The filtrate was concentrated and distilled to give methyl 2-methoxyacrylate (35 g, 68%): bp 35 C. (4 torr). This example demonstrates that methyl 2-methoxyacrylate can be prepared using superatmospheric pressure.

Statistics shows that Methyl 2,2-dimethoxypropanoate is playing an increasingly important role. we look forward to future research findings about 10076-48-9.

Reference:
Patent; Chevron Research Company; US4304928; (1981); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 18014-00-1,Some common heterocyclic compound, 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, molecular formula is C10H8Br2O4, 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.

2.63 g (10 mmol) of octyl (methyl) -aniline-4-boronic acid was dissolved in 30 ml of tetrahydrofuran, Then 2 ml of water was added, 2.12 g (20 mmol) of sodium carbonate, 1.05 g (3 mmol) of dimethyl 2,5-dibromoterephthalate, 120 mg of tetraphenylphosphine palladium, Reaction under nitrogen for 12 hours; After the reaction is completed, Add 20ml of water to extract. Separate the organic phase, The aqueous phase is extracted three times with 20 dichloromethane. The combined organic phase, Drying over anhydrous sodium sulfate. Evaporate the methylene chloride, Column chromatography (petroleum ether: dichloromethane = 5: 1), Obtained as a light yellow solid, As shown in Formula XI.

The synthetic route of 18014-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lanzhou University; Zhang Haoli; Fan Zhiping; Xu Zhuguo; Shi Zifa; (14 pag.)CN105367451; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics