Author: Jessica.F

These common heterocyclic compound, 122-72-5, name is 3-Phenylpropyl 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. Computed Properties of C11H14O2

General procedure: A general procedure for the manganese-catalysed benzylic amination is as follows. A Teflon stir bar and 5 A powdered molecular sieves (40 mg) were added in a 10 ml round-bottom flask, which was sealed with a Suba Seal rubber septum, placed under vacuum, flame-dried for 45 s to activate the molecular sieves, cooled under a purged and completely air-free argon balloon and wrapped in foil to exclude light. Once cooled, solvent (0.40 ml, 0.5 M to substrate) and substrate (0.20 mmol, 1 equiv.) were added and stirred for 10 min. Manganese(iii) perchlorophthalocyaninechloride 3 (23.1 mg, 0.020 mmol, 0.1 equiv.) and silver hexafluoroantimonate (6.9 mg, 0.020 mmol, 0.1 equiv.) were weighed in a foil-wrapped 1-dram vial in the glove box and sealed with a Teflon cap. The vial was removed from the glove box and the contents added directly to the round-bottom flask while maintaining an argon atmosphere, then stirred for 10 min at room temperature. In a 1-dram vial open to air, 2,2,2-trichloroethyl (phenyl-lambda 3-iodanylidene)sulfamate (172.2 mg,0.40 mmol, 2 equiv.) was weighed and added directly to the round-bottom flask while maintaining an argon atmosphere. The Suba Seal rubber septum was replaced by a polyethylene cap, sealed tightly, and placed in a 40 C oil bath for 8 h with stirring. Upon reaction completion, the reaction was filtered through a 1 inch silicagel plug using diethyl ether or ethyl acetate as the eluent. The crude material was concentrated and dry-loaded directly onto a silica gel column.

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

Reference:
Article; Clark, Joseph R.; Feng, Kaibo; Sookezian, Anasheh; White, M. Christina; Nature Chemistry; vol. 10; 6; (2018); p. 583 – 591;,
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These common heterocyclic compound, 175278-29-2, name is Methyl 5-fluoro-2-methylbenzoate, 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 C9H9FO2

A mixture of methyl 5-fluoro-2-methylbenzoate (0.5 g, 3.0 mmol),NBS (0.18 g, 3.0 mmol), and di-benzoyl peroxide (BPO) (36 mg, 0.15 mmol) in 1,2-dichloroethane (5 mL) was heated at 80 C for 12 huntil all starting material was consumed. The reaction was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give a crude product (0.65 g, 89%), which was used in the next step reaction without further purification.

The synthetic route of Methyl 5-fluoro-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Junli; Deng, Xiaoyan; Zhou, Siru; Wang, Na; Qin, Yujun; Meng, Liuwei; Li, Guobao; Xiong, Yuhua; Fan, Yating; Guo, Ling; Lan, Danni; Xing, Junhao; Jiang, Weizhe; Li, Qing; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 644 – 654;,
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Electric Literature of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

Intermediate 33: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate; To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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Reference of 148547-19-7,Some common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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 mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24. 88-MMOL), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 * 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methyl acrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o-tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 ML, 1M). The product is extracted with dichloromethane (2 * 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1 : 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M+1 207. The structure is confirmed by : L H NMR spectroscopy.

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63184; (2004); A1;,
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Some common heterocyclic compound, 2150-38-1, name is Methyl 3,4-dimethoxybenzoate, molecular formula is C10H12O4, 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. COA of Formula: C10H12O4

Example 1 Synthesis of 3,4-dimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 2.45 gm (61 mmol) of 60% sodium hydride, 10 gm (51 mmol) of methyl 3,4-dimethoxybenzoate, and 100 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 6.1 gm (61 mmol) of pinacolone was added dropwise. The refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 8.9 gm of the target compound as colorless needles (yield: 65%). Melting Point: 52.3-53.3 C. IR(gammaKBr, cm-1): 1602, 1521, 1470, 1446, 1365, 1299, 1266, 1218, 1188, 1131, 885, 786, 729. 1 H-NMR(CDCl3, delta): 1.26(9 H, s, t-C4 H9), 3.95(3 H, s, OCH3), 3.96(3 H, s, OCH3), 6.24(1 H, s), 6.90(1 H, d, J=8.4 Hz), 7.49(1 H, s), 7.51(1 H, d, J=8.4 Hz). Elemental analysis: Calculated (%) C: 68.16, H: 7.63; Found (%) C: 68.23, H: 7.60.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2150-38-1, its application will become more common.

Reference:
Patent; Kao Corporation; US5146002; (1992); A;,
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Reference of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, 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.

To a reactor under nitrogen atmosphere was added a toluene solution of ester 6 (LOO Wt, 1.0 eq), methyl 2-fluorobenzoate (0.91 Wt, 0.75 Vol 1.10 eq)5 and THF (0.53 Wt, 1.8 Vol). The solution was cooled to below -70 C. Lithium hexamethyldisilazide (LiHMDS, 1.0M in THF, 7.6 Wt, 8.6 Vol, 1,6 eq) was added at such rate that the internal temperature does not exceed -60°C.. After completion of the LiHMDS addition, the mixture was warmed (rate between 10-20C/h) and stirred at -40C for 1h. The reaction was monitored by GC (Conversion Target >95percent). If after 4h the conversion is still under targeted amount, additional LiHMDS 1M in THF was added (1.1 eq based on unreacted starting material). After achieving the target conversion, the internal temperature was raised (rate between 20-30°C/h) to 15 to 20 °C. 25 wtpercent aqueous ammonium chloride (1,7 Wt, 1.6 Vol) was added to the reactor keeping the internal temperature below 0 °C Upon completion of the addition, the mixture was warmed to ?0°C, and transferred to a vessel containing 25 wtpercent aqueous ammonium chloride (4.4 Wt, 4.1 Vol) and water (1.1 Wt, 1.1 Vol).The mixture was stirred for at least 30 min at 20-25 °C. The lower aqueous layer was removedand the organic layer was washed with 20 wt percent aqueous sodium chloride (3.0 Wt, 1.4 Vol). The mixture was stirred for at least 15 minutes then allowed to settle. The lower aqueous layer was removed. The organic phase was concentrated under reduce pressure (Jacket < 25 °C) untildistillation ceases. Toluene (6.6 Wt, 6.7 Vol) was added and the resulting mixture was washedwith water (3.0 Wt, 3.0 Vol), stirred for at least 15 min, then allowed to settle. The organics werewashed with water (3.0 Wt, 3.0 Vol) until pH is constant at pH=78. The organic phase was washed with 20percent aqueous sodium chloride (3.0 Wt, 1.4 Vol). The organic phase was concentrated under reduced pressure (jacket <25°C) to afford ketoester 11 (2.1 Wt) as an orangeoil. The synthetic route of 394-35-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ???????????????????????????; ? Buranko; Kimu ?; Chan ?; ?; Yoshizawa Kazuhiro; (94 pag.)JP2016/121177; (2016); A;,
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Related Products of 54535-22-7, A common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, 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.

j00330J A 1 L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4- Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHU, Cathy; DOKOU, Eleni; HASELTINE, Eric L.; MOSKOWITZ, Samuel; OVERHOFF, Kirk A.; ROBERTSON, Sarah; WALTZ, David; (204 pag.)WO2019/10092; (2019); 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. 49851-36-7, name is Methyl 2-(2-aminophenyl)acetate hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of Methyl 2-(2-aminophenyl)acetate hydrochloride

To a solution of methyl 2-(2-aminophenyl)acetate hydrochloride (CAS 49851-36-7) (0.50 g, 2.5 mmol) in DMF (24.8 ml) at 0 C was added NBS (0.441 g, 2.48 mmol) and this was stirred at 0 C. After 10 minutes the reaction was quenched with saturated aqueous sodium bicarbonate, extracted with EtOAc, washed with water, dried over MgS04, filtered and concentrated. This was purified by flash chromatography (0-15% EtOAc:DCM) to provide the title compound. MS (ESI+) m/z 244.1 , 246.1 (M+H).

The synthetic route of 49851-36-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BELANGER, David B.; FLOHR, Stefanie; GELIN, Christine Fang; JENDZA, Keith; JI, Nan; LIU, Donglei; LORTHIOIS, Edwige Liliane Jeanne; KARKI, Rajeshri Ganesh; MAINOLFI, Nello; POWERS, James J.; RANDL, Stefan Andreas; ROGEL, Olivier; VULPETTI, Anna; YOON, Taeyoung; WO2015/9977; (2015); A1;,
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Electric Literature of 18448-47-0, 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. 18448-47-0, name is Methyl cyclohex-1-enecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: Cyclohex-l-en-l-ylmethanol To a solution of methyl 1-cyclohexene-l-carboxylate (1.50 mL, 11.0 mmol) in DCM (30 mL) was added diisobutylaluminum hydride (1M solution in toluene; 25 mL, 25 mmol) at -78 C and the mixture was stirred for 1 h. TLC (3:1 hex:EtOAc) showed that the reaction was then complete. The mixture was quenched with methanol (10 mL) and IN NaOH (10 mL) and then was allowed to stir at rt for 2.5 h. The mixture was extracted with DCM (3x). The combined organic layers were washed with brine, dried over MgSCt, filtered and concentrated to give cyclohex-l-en-l-ylmethanol (1.3 g, 100%).

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 cyclohex-1-enecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; DUFFEY, Matthew, O.; ENGLAND, Dylan, B.; HU, Zhigen; ITO, Mitsuhiro; LANGSTON, Steven, P.; MCINTYRE, Charles; MIZUTANI, Hirotake; XU, He; WO2015/2994; (2015); A2;,
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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 139102-34-4 as follows. Quality Control of Methyl 4-bromo-2-methoxybenzoate

A solution of 4-bromo-2-methoxybenzoic acid methyl ester (0.1 mol) and tetrahydro- 2H”-pyran-4-amine (0.3 mol) in 1 -methyl-2-pyrrolidinone (800 ml) was stirred at 400C. Cs2CO3 (0.2 mol) was added. The reaction mixture was stirred for 5 minutes. Pd2(dba)3 (0.002 mol) and BINAP (0.003 mol) were added. The reaction solution was degassed by applying alternating nitrogen atmosphere and vacuum. The reaction mixture was stirred overnight at 110C. The 1 -methyl-2-pyrrolidinone solvent was evaporated. The residue was purified by high-performance liquid chromatography. The product fractions were collected and the solvent was evaporated, yielding 13 g of intermediate (29).

According to the analysis of related databases, 139102-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2009/62990; (2009); A2;,
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