Category: esters-buliding-blocks

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. 618-89-3, name is Methyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 3-bromobenzoate

I. Methyl 3-benzylbenzoate; [00306] A solution of 3-bromomethylbenzoate (500 mg, 2.18 mmol), phenylboronic acid (290 mg, 2.40 mmol), PdCl2(PPh3)2 (46 mg, 0.07 mmol) and K3PO4 (1.16 g, 5.45 mmol) in DMF (10 mL) and water (2 mL) was heated at 8O0C for 1 hr and then cooled to room temperature and diluted with EtOAc. The reaction mixture was washed with water (3 times) and saturated NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with 1 :19 EtOAc:hexanes to give a colorless oil (353 mg, 72%).

The synthetic route of 618-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENCYSIVE PHARMACEUTICALS, INC.; WO2008/79371; (2008); A1;,
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These common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, 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. Computed Properties of C4H7BrO2

Add p-chlorodiphenyl disulfide (0.5 mmol) to a 10 mL reaction tube.Methyl alpha-bromopropionate (1.0 mmol),Zinc powder (2.0 mmol) solvent toluene (2 mL) and dinuclear Schiff base titanium perfluorooctanesulfonic acid complex (X=OSO2C8F17)(0.04 mmol), stirred for 4 h at 25C. Spin dry after the reaction is over.The residue was extracted with ether three times and the filtrate was evaporatedThe crude product was separated by silica gel column chromatography.This gave methyl 2-p-chlorophenylthiopropionate as a colorless oily liquid in a yield of 86%.

The synthetic route of Methyl 2-bromopropanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanxi Medical University; Li Ningbo; Wang Lingxiao; Wang Haojiang; Zhao Wenjie; (13 pag.)CN107722049; (2018); A;,
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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 153559-48-9 as follows. Product Details of 153559-48-9

Example 3: Preparation of bexaroteneTo suspension of methyl 4-[l-(5,6,7,8-tetrahydro-3, 5,5,8, 8-pentamethyl-2-naphthalenyl)-l- ethenyljbenzoate (100 g) in methanol (1000 ml), 5N aqueous potassium hydroxide (170 ml) was added at 25-30C and the reaction mixture was refluxed for 8 hours. After completion of reaction (monitored by HPLC), reaction mass was cooled to 35-40 C and washed with 50% ethyl acetate: n-heptane mixture (2 x 500 ml). The organic layer was discarded and the aqueous layer was cooled to 10-15 C. Thereafter pH of aqueous layer was adjusted to 1-2 by addition of concentrated hydrochloric acid (100 ml). The resulting mixture was then stirred at 20-25C, stirred for 1 hour and precipitated solid was filtered. The resulting solid was slurry washed with demineralized water (100 ml), centrifuged and dried to give 84.6 g of title compound having purity 98.89 %, none of the impurities C, D, E, F were detected by HPLC

According to the analysis of related databases, 153559-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IND-SWIFT LABORATORIES LIMITED; BHIRUD, Shekhar, Bhaskar; SARIN, Gurdeep, Singh; SHARMA, Bimal, Kumar; GERA, Pardeep; WO2011/141928; (2011); A1;,
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Related Products of 41658-03-1, These common heterocyclic compound, 41658-03-1, name is Ethyl 3-bromopropiolate, 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: A dry and argon flushed Schlenk-flask, equipped with a magnetic stirring bar and a rubber septumwas charged with 1,8-bis(butylthio)-3,6-dichloro-2,7-naphthyridine (1.0 equiv) in THF. After cooling to-40 C, a solution of TMPLi (1 M in THF, 1.2 equiv) was slowly added. The reaction mixture wasstirred for 30 min at the same temperature. Then, the corresponding electrophile (1.2 equiv) wasadded and the solution was stirred at -40 C until complete conversion of the starting material(detected by GC-analysis of reaction aliquots).

The synthetic route of 41658-03-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Greiner, Robert; Blanc, Romain; Petermayer, Christian; Karaghiosoff, Konstantin; Knochel, Paul; Synlett; vol. 27; 2; (2016); p. 231 – 236;,
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Electric Literature of 52787-14-1,Some common heterocyclic compound, 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, molecular formula is C11H12O4, 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.

A 50-mE round-bottom flask was charged with methyl 4-(2-methoxy-2-oxoethyl) benzoate (1 g, 4.80 mmol), (dimethoxymethyl)dimethylamine (571 mg, 4.79 mmol) and N,N-dimethylformamide (15 mE). The resulting solution was stirred for 4 h at 60 C. Afier cooling to 23 C., the reaction was quenched with water (30 mE) and the product was extracted with ethyl acetate (3×30 mE). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by colunm chromatography eluting with ethyl acetate/petroleum ether (1:1 v/v) to afford methyl 4-(1 -(dimethylamino)-3- methoxy-3-oxoprop- 1 -en-2-yl)benzoate as a yellow solid (800 mg, 63%). ECMS: (ESI) mlz 264 [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 Methyl 4-(2-methoxy-2-oxoethyl)benzoate, its application will become more common.

Reference:
Patent; Forma Therapeutics, Inc.; Ioannidis, Stephanos; Talbot, Adam Charles; Follows, Bruce; Buckmelter, Alexandre Joseph; Wang, Minghua; Campbell, Ann-Marie; Schmidt, Darby Rye; Guerin, David Joseph; Caravella, Justin A.; Diebold, R. Bruce; Ericsson, Anna; Lancia, JR., David; (225 pag.)US2016/185785; (2016); A1;,
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Electric Literature of 3469-00-9, 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. 3469-00-9, name is Methyl Diphenylacetate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4.2 General procedures: A. Microwave. Neat samples of amine (1.00 mmol) and carboxylic derivative (methyl ester or acid, 1.00 mmol) and DABAL-Me3 (202 mg, 0.8 equiv) were placed in a 5 mL microwave vial and dry THF added (1 mL) under a blanket of argon. For coupling partners containing acidic hydrogens additional DABAL-Me3 (total of 410 mg, 1.6 equiv) was used. The vial was promptly capped and placed in a CEM Discover microwave reactor. After irradiation (290 W, 130 C, 8 min) and programmed cool down (ca. 20 min). The reactions were quenched by cautious addition of HCl (2 M, 4 mL) or aqueous solutions of Rochelle salt (saturated potassium sodium tartrate, 4 mL) (CARE: methane liberated). Extraction with dichloromethane, drying (MgSO4) and evaporation frequently provided the pure products directly. If purification was required column chromatography 3:2 to 2:3 hexane:EtOAc was used for amides lacking highly polar functional groups (CH2Cl2 with 2 % v/v MeOH was used for amides bearing pendant amines, alcohols and other polar functional groups).

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

Reference:
Article; Dubois, Nathalie; Glynn, Daniel; McInally, Thomas; Rhodes, Barrie; Woodward, Simon; Irvine, Derek J.; Dodds, Chris; Tetrahedron; vol. 69; 46; (2013); p. 9890 – 9897;,
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Adding a certain compound to certain chemical reactions, such as: 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, 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 816-27-3, name: Ethyl 2-ethoxy-2-iminoacetate

To a solution of cis-1-amino-3-[tert-butyl(dimethyl)silyl]oxy-5-phenyl-pyrrolidin-2-one (9.5 g, 31.0 mmol) in ethanol (250 mL) was added ethyl 2-ethoxy-2-imino-acetate (6.7 g, 46.5 mmol). The reaction mixture was stirred at 60 C. for 6 h and subsequently concentrated under reduced pressure to afford crude ethyl 2-[[cis-3-[tert-butyl(dimethyl)silyl]oxy-2-oxo-5-phenyl-pyrrolidin-1-yl]amino]-2-imino-acetate as a yellow oil (10.6 g, 84%), used in the next step without further purification. LCMS RT=2.106 min, m/z=406.2 [M+H]-. LCMS (10 to 80% acetonitrile in water+0.1% ammonia water over 3.0 mins) retention time 2.106 mm, ESI+ found [M+H]=406.2.

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 2-ethoxy-2-iminoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
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79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C9H9BrO2

(2) A suspension of 1.19 g (9.46 mmol) of phenylboronic acid, 1.97 g (8.60 mmol) of methyl 5-bromo-2-methylbenzoate, 4 mg (0.017 mmol) of palladium (II) acetate, 2.97 g (21.5 mmol) of potassium carbonate, and 2.77 g (8.6 mmol) of tetrabutylammonium bromide in 20 ml of water was vigorously stirred under a stream of nitrogen, and stirred at 70 C. under an atmosphere of nitrogen for 1 hour. Water was added to the reaction mixture and it was extracted with tert-butyl methyl ether. The organic layer was dried and concentrated. The residue (1.9 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=30:1) to obtain 1.65 g (7.29 mmol) of methyl 5-phenyl-2-methylbenzoate as an oil.

The synthetic route of 79669-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6489487; (2002); B1;,
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Application of 89-71-4, 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 89-71-4 as follows.

A mixture of methyl o-toluate (13.5 g, 89.9 mmol), NBS (17.6 g, 98.9 mmol), and benzoyl peroxide (50 mg, 0.2 mmol) in carbon tetrachloride (250 mL) was heated at reflux over the weekend. The reaction mixture was allowed to cool, and it was then filtered. The solvents were evaporated under reduced pressure and the residue was purified by chromatography, eluting with 3% ethyl acetate/hexanes to give 2-bromomethyl-benzoic acid methyl ester (7.7 g, 37%) as a white solid. 1HNMR (CDCl3): delta 7.97 (dd, J=1.5 Hz, 8.0 Hz, 1H), 7.49 (m, 2H), 7.38 (dt, J=1.5 Hz, 8.0 Hz, 1H), 4.96 (s, 2H), 3.94 (s, 3H). MS (APCI+): 231 (100), 229 (93).

According to the analysis of related databases, 89-71-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chu, Chang An; Gillespie, Paul; Tilley, Jefferson Wright; US2004/266856; (2004); 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 40546-94-9 as follows. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Example 1[149] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid; [150](H) (HI)[152] [153] A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 55-65C for 2-3 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1-2 hr. After the completion of addition, reaction mixture was stirred at same temperature for 1-2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 70-800C for 3-5 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 1-2 hrs, then filtered &; washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 55-600C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid.[154] (Yield: 0.71 kg, 83%). [155] HPLC Purity: >; 95 %.

According to the analysis of related databases, 40546-94-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALEMBIC LIMITED; PONNAIAH, Ravi; DESAI, Sanjay; SHAH, Chankrakant Chunilal; PATEL, Kalpesh Shantibhai; PAREKH, Viral Maheshbhai; WO2010/92500; (2010); A2;,
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