Author: Jessica.F

Reference of 87808-49-9, 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. 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) A suspension of the Compound 2 (4.0 g), the Compound 3 (3.52 g), [1,1?-bis(diphenylphosphino) ferrocene]palladium(II) dichloromethane adduct (1.43 g), and potassium carbonate (7.24 g) in N,N-dimethylformamide (80 mE) was stirred at 80 C. under a nitrogen atmosphere for 6 hours. To the reaction mixture was added diethyl ether (200 mE), and the resulting mixture was stirred, and then the resulting insoluble matters were removed by filtration. To the resulting filtrate were added water and ethyl acetate, and the resulting mixture was stirred, and then extracted with ethyl acetate. The resulting organic layers were washed with water and saturated brine, then dried, and concentrated under reduced pressure. The resulting residues were purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 80:20) to give the Compound 4 (2.78 g) as a pale yellow viscous material. MS (APCI): mlz 191 [M+H](3) To

The synthetic route of Methyl 2-bromo-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; SATO, Atsushi; IMASHIRO, Ritsuo; TSUJISHIMA, Hidekazu; TANIMOTO, Kouichi; YAMAMOTO, Yasuo; NAKANE, Tetsu; TOSHIKAWA, Chihiro; (118 pag.)US2018/258076; (2018); A1;,
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148438-00-0, name is Methyl 3-(trifluoromethoxy)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. category: esters-buliding-blocks

Reference Example 6 2.5 M Butyl lithium in hexane (18.5ml) was added under an inert atmosphere to a solution of 3-fluorobenzoic acid (3.0g) in dry tetrahydrofuran at -75oC. The reaction mixture was stirred at -78oC overnight. A solution of methyl 3-trifluoromethoxybenzoate (4.6g) in dry tetrahydrofuran was added and after 2 hours the reaction mixture was allowed to warm to -20oC. 2N hydrochloric acid was added, the mixture and the organic layer was separated and dried (MgSO4). Evaporated the solvent and triturated the residue with hexane to yield 3-fluoro-2-(3-trifluoromethoxybenzoyl)benzoic acid (4.3g) as a white solid, m.p. 135-140oC.

The synthetic route of 148438-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RHONE POULENC AGRICULTURE LTD.; EP634404; (1995); A1;,
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Reference of 1462-12-0, 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. 1462-12-0, name is Diethyl 2-ethylidenemalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of diethyl ethylidene malonate A (96 g; 0.51 mol), S-methyl isothiourea (71.1 g; 0.79 mol) and triethylamine (80 mL) in 530 mL of abs. ethanol, was refluxed for 3 h under magnetic stirring. The reaction mixture was filtered, and the ethanol concentrated under vacuum, water was added (400 mL) and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and concentrated. The crude reaction mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=7/3) to yield compound B (63.7 g; 55%) as a pure solid. 1H-NMR (400 Mhz, DMSO-d6), ppm: 1.16 (d, j=6.6 Hz, 3H); 1.17 (t, j=7.2 Hz, 3H); 3.29 (d, j=10.5 Hz, 1H); 3.84 (dq, j=6.6, 10.5 Hz, 1H); 4.21 (m, 2H);

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, Diethyl 2-ethylidenemalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmacia Italia S.p.A.; US2004/9993; (2004); 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. 587-47-3, name is Ethyl 2-(3-fluorophenyl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C10H11FO2

To a solution of ethyl 2-(3-fluorophenyl) acetate (2.0 g, 10.98 mmol) in THF (20 mL), was added potassium bis(trimethylsilyl) amide (1.0 M solution in THF; 12.1 mL, 12.1 mmol), dropwise. The reaction mixture was stirred at rt for 15 mi and then 2-bromo-1,1-diethoxyethane (2.38 g, 12.1 mmol) was added, dropwise. The mixture was heated at 45 C for 1 h, then was cooled to 0 C and was treated with saturated NH4C1 solution (10 mL) and water (50 mL). The mixture was extracted with MTBE (3 x 50 mL). The combined organic phase was washed with water and brine, dried over Na2SO4 and concentrated. This product was taken up in water (7.5 mL) and was treated with a mixtureof chloroform (25 mL) and TFA (25 mL) and was stirred at 0 C to 10 C for 2 h. The reaction mixture was poured into a mixture of 1M solution of K2C03 (125 mL) and dichloromethane (200 mL). Solid K2C03 was added until pH 7.5 was reached. The organic layer was separated, washed with water and brine, dried over Na2504 and concentrated. The crude product was purified by flash chromatography (10% – 15%EtOAc/hexanes gradient) to give Intermediate 1OA (0.95 g, 4.24 mmol, 39% yield).GCMS m/z = 224; NMR (300 MI-Tz, chloroform-d) oe ppm 9.78 (s, 1 H), 7.35 – 7.26 (m, 1H), 7.12 – 6.94 (m, 3 H), 4.23 -4.04 (m, 3 H), 3.40 (dd, J = 9.8, 18.6 Hz, 1 H), 2.83 (dd, J= 4.7, 18.3 Hz, 1 H), 1.23 (t, J = 7.1 Hz, 3H).

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; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
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Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, 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 Preparation of the compound of formula (I) (referred as ACGET61 ) Formula (I) In a round-bottomed flask equipped with an efficient condenser and a magnetic stirrer, Ri (MW: 175.088; 4.43g) and R2 (MW:132.16; 3.347g) are added in an 1 :1 molar ratio. NH4CI (443mg) is then added as catalyst (10% by weight with respect to Ri). The mixture is heated at 150C for 45h and it assumes a deep green / dark purple colour. The disappearance of the reagent is monitored by TLC (AcOEt: Hexane 1 :2) using ninhydrin as detecting agent (prepared dissolving 200mg ninhydrin in 150 ml EtOH). When the reagent is completely disappeared, the reaction mixture is cooled and the residue is dissolved in DCM, washed three times with HCI 3N then with water till neutral pH. The crude product thus obtained is purified by column chromatography eluting with a gradient of AcOEt: Hexane (from 1 : 10 to 1 :1 ). The pure product (ACGET61 , MW 275.1 1 ) is obtained as a white / light pink solid in 64% yield.

The synthetic route of 29006-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIO FARMACEUTICO C.T. S.R.L.; CACCIAGLIA, Roberto; LOCHE, Antonella; (33 pag.)WO2017/21438; (2017); 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. 55099-31-5, name is Ethyl 10-bromodecanoate, A new synthetic method of this compound is introduced below., SDS of cas: 55099-31-5

1f. Preparation of Compound 6 A 3-neck 300 mL round-bottomed flask equipped with a reflux condenser, magnetic stir bar and a nitrogen inlet was charged with 4 g (1 equivalent) of 2-hydroxybenzonitrile, absolute ethanol 140 mL, and 12.54 mL (1 equivalent) of sodium ethoxide. This mixture was stirred at 25 C. for 15 minutes. Ethyl 10-bromodecanoate (9.4 g, 1 equiv.) 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 ethyl acetate (300 mL) and washed with 1/2 saturated NaHCO3 (2*100 mL), H2O (1*100 mL) and brine (1*50 mL). The organic layer was dried to give 10 g of the crude ester. The crude material was then dissolved in ethanol (100 mL) and water (20 mL). LiOH (3.3 g) was added and the resulting mixture was heated to reflux (75 C.) for 3 hours. The solution was cooled and the solvent removed. 20 mL of H2O was added and the aqueous solution was acidified to a pH of about 3 with concentrated HCl. The solution was transferred to a 4 C. refrigerator to cool. A tan colored solid began to precipitate. 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) to give 7.1 g of the product, 10-(2-cyanophenoxy)decanoic acid (78% yield). Melting point: 82-84 C. Molecular Formula with water: C17H23NO3*0.0532. Combustion analysis: %C: 70.33 (calc’d), 69.82 (found); %H: 8.02(calc’d), 7.89(found); %N: 4.82 (calc’d), 4.82 (found).

The synthetic route of 55099-31-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Moye-Sherman, Destardi; Gschneidner, David; US2003/199427; (2003); A1;,
Ester – Wikipedia,
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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. 915213-54-6, name is Ethyl 2-(4,4-difluorocyclohexyl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C10H16F2O2

To a solution ofethyl 2-(4-oxocyclohexyl)acetate(0.4 g) inDCM(5 mL) was addedDeoxo-Fluor(0.881 mL) andEtOH(0.038 mL). The reaction mixture was stirred at rt for 16 h and then diluted with sat. NaHCO3and EtOAc. The organic phase was washed with water, sat. NaCl and dried over anhydrous Na2SO4, filtered and dried to yield ethyl 2-(4,4-difluorocyclohexyl)acetate (0.4 g). To a solution ofethyl 2-(4,4-difluorocyclohexyl) acetateinTHF/MeOH(2 mL) was added 1NNaOH(1 mL), and the reaction mixture was stirred at rt for 16 h. The reaction mixture was concentrated, then diluted with EtOAc and acidified with 1N HCl. The organic phase was washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated to yield2-(4,4-difluorocyclohexyl)acetic acidas ayellowsolid.1H NMR (400 MHz, DMSO-d6) ppm 12.13 (1H, br. s.), 2.06-2.28 (3H, m), 1.92-2.03 (1H, m), 1.72-1.91 (4H, m), 1.31-1.48 (1H, m), 1.10-1.31 (2H, m).

The synthetic route of 915213-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); 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. 111-79-5, name is Methyl non-2-enoate, A new synthetic method of this compound is introduced below., Recommanded Product: 111-79-5

PREPARATION 2 4-Nitro-beta-hexyl-1H-imidazole-1-propanoic acid methyl ester The title intermediate was prepared by combining 5.0 grams of 4-nitroimidazole, 8.26 g of methyl 2-nonenate, 4.08 g of sodium bicarbonate, and 200 ml of dimethylformamide and heating the mixture at 80 C. for 18 hours. After cooling, the mixture was poured into water and extracted into ethyl acetate. The organic layer was concentrated in vacuo and the residue purified by HPLC over a silica column eluding with ethyl acetate. The appropriate fractions were combined and concentrated in vacuo to provide 2.2 g of the desired titled intermediate. Analysis for C13 H21 N3 O4: Calc.: C, 55.11; H, 7.47; N, 14.83; Found: C, 55.37; H, 7.37; N, 14.58.

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; Eli Lilly and Company; US5073566; (1991); A;,
Ester – Wikipedia,
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Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, 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.

Lithium diisopropylamide was prepared by addition of n-butyllithium (2.5 M in hexanes, 11.7 mL, 58.8 mmol) to diisopropylamine (9.7 mL, 70.6 mmol) in dry tetrahydrofuran (100 mL) at -78 C. Stirring was continued for 15 min at -78 C before methyl 4-methoxybutanoate (6.84 g, 51.8 mmol) was added to the reaction mixture. Stirring was continued for 20 min at -78C and benzaldehyde (5g, 47.1 mmol) in tetrahydrofuran (20 mL) was added, and the reaction mixture allowed to warm slowly to room temperature. Stirring was continued for 2 hours, water (50 mL) was added under stirring and the mixture was extracted with ether (3 x 50 mL). The combined organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated under reduced pressure to afford methyl 2-(hydroxy(phenyl)methyl)-4-methoxybutanoate (10.7 g, 44.9 mmol) in 95% yield. LCMS (ESI+): 261.1 (M+Na).

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-methoxybutanoate, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; AUDIA, James, Edmund; COTE, Alexandre; DUPLESSIS, Martin; GEHLING, Victor, S.; HARMANGE, Jean-christophe; VASWANI, Rishi, G.; (274 pag.)WO2016/172496; (2016); A1;,
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Synthetic Route of 144267-97-0, 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 144267-97-0 as follows.

5-Fluoro-6-[5-(benzyloxy)benzifnid zol-l-yl]-l,3-dihvdro-l-hydwxy-2,l- benzoxaborole Preparation of ethyl 2-bromo-5-fluoro-4-(4-methoxy-2-nitrophenylamino) benzoate[0242] To a solution of 4-methoxy-2-nitroaniline (6 g, 22.6 mmol, 1 eq) and ethyl 2-bromo-4,5-difluorobenzoate (3.8 g, 22.6 mmol, 1 eq) in dry DMF (225 mL) was added CS2CO3 (12.7 g, 33.9 mmol, 1.5 eq) under N2 protection. The mixture was heated to 100C for 4h. TLC analysis showed there was no starting material remained. The mixture was mixed with 300mL water. The mixture was extracted with EA (2 x 100 mL) and the organic layer separated was washed with 0.5N HCl, water, brine and dried over anhydrous Na2S04. The mixture was filtered and the filtrate was concentrated. The solid was purified by recrystallization with EA/PE to give 6 g of product (yield 65%).

According to the analysis of related databases, 144267-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ZHANG, Yong-kang; ZHOU, Huchen; DING, Charles; PLATTNER, Jacob, J.; FREUND, Yvonne; WO2011/63293; (2011); A1;,
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