Tag: M.W=200-300

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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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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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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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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Reference of 59247-47-1, 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. 59247-47-1, name is tert-Butyl 4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 100 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[l-cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5- yl]methoxy]-2-azabicyclo[2.2.1]heptane 621 (45 mg, 0.12 mmol, 1.00 equiv.), toluene (20 mL), tert-butyl 4-bromobenzoate (45.7 mg, 0.18 mmol, 1.50 equiv), BINAP (15 mg, 0.02 mmol, 0.20 equiv.), Cs2CO3 (116 mg, 0.36 mmol, 3.00 equiv.), and Pd2(dba)3 (11 mg, 0.01 mmol, 0.10 equiv.). The resulting mixture was heated for at 1 10¡ãC for 2 days. After cooling to room temperature, solids were filtered out, and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 : 10 to 1 :5, and to 1 :3). Removal of solvents afforded tert-butyl 4-[(1S,4S,5R)-5-[[l- cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan- 2-yl]benzoate 70a (40 mg, 61percent) as a light brown oil.

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Application of 849758-12-9, 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. 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 4-bromo-3-fluoro-benzoic acid methyl ester (1 g, 4.29 mmol), hydrazine hydrate (2.2 ml_, 42.9 mmol) and MeOH (20 ml_) was heated at 70 C for overnight. Concentrated, diluted with EtOAc (300 ml_) and washed with water (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated give the desired product 2AR (0.9 g, 90%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-3-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
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Reference of 23877-12-5,Some common heterocyclic compound, 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, molecular formula is C8H15BrO2, 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.

Scheme 1. A solution of ethyl-(6-triisopropylsilanylsulfanyl-1, 2,3, 4- tetrahydro-naphthalen-2-yl)-carbamic acid 4-trifluoromethoxy-phenyl ester (260.0 mg; 0.46 MMOL) and tert-butyl 11-BROMOISOBUTYL RATE (130 uL, 0.69 MMOL) in anhydrous THF (2 mL) was cooled to 0 C, a 1.0 M solution of TBAF (690 uL, 0.69 MMOL) was added, then the reaction was warmed to RT, stirred for 1 h, and then diluted with water, extracted with Et20 (3 times). The combined organic extracts were dried over NA2SO4, and the solvent removed under reduced pressure. The crude residue was purified by flash chromatography eluting with Hexane-EtOAc (7: 1) to provide 229.2 mg (90%) of 2- {6- [ETHYL- (4-TRIFLUOROMETHOXY- PHENOXYCARBONYL)-AMINO]-5, 6,7, 8-TETRAHYDRONAPHTHALEN-2-YLSULFANYL}-2-METHYL- propionic acid tert-butyl ester as a light-color oil. 1H NMR (300 MHz, CDCI3) : S 6.95-7. 28 (m, 7 H), 4.34 (m, 1H), 3.41 (m, 2H), 2.96 (m, 2H), 2.91 (m, 2H), 3.41 (m, 2H), 2.06 (m, 2H), 1.44 (s, 6H), 1.42 (s, 9H), 1.28 (m, 3H) LC/MS: C28H34F3NO5SNA : m/z 576 (M+NA)

The synthetic route of 23877-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2004/37779; (2004); A1;; ; Patent; JANSSEN PHARMACEUTICA, N.V.; Demarest, Keith, T.; WO2004/37778; (2004); A1;,
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Synthetic Route of 2178-24-7,Some common heterocyclic compound, 2178-24-7, name is Ethyl (2-bromophenyl)acetate, molecular formula is C10H11BrO2, 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 1(4′-Methylbiphenyl-2-yl)acetic acid a) Ethyl (4′-methylbiphenyl-2-yl)acetateTo a mixture composed of 243.1 mg (1 mmol) of ethyl 2-(2-bromophenyl)- acetate, 3.7 ml of toluene, 57.8 mg (0.05 mmol) of tetrakis(triphenylphosphine)- palladium and 127.2 mg (1.2 mmol) of anhydrous sodium carbonate are added EPO 169.9 mg (1.25 mmol) of 4-methy.phenylboronic acid, followed by addition of 2.21 ml (0.055 mmol) of methanol. The reaction medium is heated at 85C for 16 hours with stirring. After cooling, 10 ml of water and 8 ml of ethyl acetate are added with stirring, and the mixture is then filtered through a fluted filter paper. The organic phase is recovered and the aqueous phase is extracted again with ethyl acetate.The combined organic phases are washed with water (2 x 10 ml), dried over Na2SO4 and then concentrated to give 310 mg of oil, which is purified by flash chromatography on a column of silica, in a dichloromethane/heptane mixture (1 :1). 201 mg of a colourless oil are obtained.Yield: 79%NMR (CDCI3): 1.2 (t, J=7.2 Hz, 3H); 2.5 (s, 3H); 3.7 (m, 2H), 4.1 (q, J=7.2 Hz, 2H); 7.3 (m, 8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl (2-bromophenyl)acetate, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; WO2006/58592; (2006); A1;,
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Application of 17100-65-1,Some common heterocyclic compound, 17100-65-1, name is Methyl 2-bromo-4-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.

(0580) Methyl 2-bromo-4-methoxybenzoate (20 g, 0.082 mol) was dissolved in N,N-dimethylformamide (100 mL), and cuprous cyanide (10.95 g, 0.123 mol) was added. (0581) The reaction was carried out at 150 C. for 4 h. The mixture was cooled, and was poured into saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate (150 mL¡Á3). The organic phases were combined, dried with anhydrous sodium sulfate, filtrated, and concentrated. The crude product was purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:1) to get the title compound (9.8 g, yield: 62%).

The synthetic route of 17100-65-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); A1;,
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