Month: July 2021

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. 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 4-methyl-3-(trifluoromethyl)benzoate

To a solution of 4-methyl-3-trifluoromethylbenzoic acid (1.71 g, 8.37 mmol) in DMF (20 mE) was added potassium carbonate (1.39 g, 10.1 mmol) and the reaction mixture was stirred at room temperature for five minutes. lodomethane (0.78 mE, 12.5 mmol) was added and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine (x2). The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated at reduced pressure to afford methyl 4-methyl-3-trifluo- romethylbenzoate. The material was dissolved in carbon tetrachloride (10 mE) and treated sequentially with N-bromosuccinimide (2.74 g, 15.4 mmol) and benzoyl peroxide (catalytic) and heated at 80 C. for 18 hours. The mixture allowed to cool and diluted with water. The mixture was poured through a hydrophobic fit and the solvent evaporated at reduced pressure to afford methyl 4-(dibromom- ethyl)-3-trifluoromethylbenzoate. The material was dissolved in acetone/water (25 mE/S mE) and silver nitrate (2.38 g, 14.0 mmol) added. The reaction mixture was stirred at room temperature for 72 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was dissolved acetone/ water (25 mE/S mE) and silver nitrate (2.38 g, 14.0 mmol) added. The reaction mixture was stirred at room temperature for 24 hours. The suspension was filtered through a pad of celite and the filtrate diluted with ethyl acetate. The solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (eluent-100% i-hexane to 8:1 i-hexane/ethyl acetate) to afford the title compound (0.537 g, 33%). 1H NMR (400 MHz, CDC13); oe 10.46-10.45 (m,1H), 8.46 (s, 1H), 8.35 (d, J=8.2 Hz, 1H), 8.20 (d, J=8.2 Hz,1H), 4.00 (s, 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; CHIESI FARMACEUTICI S.p.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; KNIGHT, Chris; SCHMIDT, Wolfgang; (176 pag.)US2016/235734; (2016); A1;,
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Synthetic Route of 4891-38-7, 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. 4891-38-7, name is Methyl Phenylpropiolate, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A representative procedure of skeleton 1 is as follows: CuI (190 mg, 1.0 mmol), Et3N (200 mg, 2.0 mmol) and different alkynes 6a-h (1.0 mmol) were added to a solution of compound 5a (110 mg, 0.4 mmol) in anhydrous DMF (4 mL) at rt. The reaction mixture was stirred at 80 C for 2 h, then cooled to rt. Saturated NaHCO3(aq) (5 mL) was added to the reaction mixture and the solvent was evaporated under reduced pressure. The residue was extracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine,dried, filtered and evaporated under reduced pressure to afford crude product. Purification on silica gel (hexanes/EtOAc = 2/1-1/2) afforded compounds 1a-h.

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

Reference:
Article; Chang, Meng-Yang; Tai, Hang-Yi; Synthetic Communications; vol. 43; 24; (2013); p. 3363 – 3372;,
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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 121-98-2 as follows. Recommanded Product: Methyl 4-methoxybenzoate

To a cooled (-20 C) solution of 4-methoxybenzoic acid methyl ester 11 (3.00 g, 18.1 mmol) in MeCN (30 mL) was added HBF4·Et2O (3.22 mL, 19.9 mmol) and then slowly added NBS (3.54 g, 19.9 mmol) under less than -10 C. After the addition, the cooling bath was removed and the reaction mixture was allowed to warm up to room temperature, and stirred for 23 h. Saturated NaHSO3 solution was then added, and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated NH4Cl solution and brine, dried over Na2SO4, and then concentrated in vacuo. Purification by silica gel column chromatography (hexane/EtOAc = 5/1) gave 12 (4.35 g, 17.7 mmol, 98%) as a colorless powder;

According to the analysis of related databases, 121-98-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ogura, Tetsuhiro; Usuki, Toyonobu; Tetrahedron; vol. 69; 13; (2013); p. 2807 – 2815;,
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Adding a certain compound to certain chemical reactions, such as: 6627-89-0, name is tert-Butyl phenyl carbonate, 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 6627-89-0, Formula: C11H14O3

Intermediate 130; 1,1-dimethylethyl (2-amino-2-methylpropyl)carbamate; To a solution of 2-methyl-1 ,2-propanediamine (300 mg, 3.40 mmol) in ethanol (15 ml) was added phenyl-tBu-carbamate (1.32 g, 6.80 mmol). The reaction mixture was stirred at 800C overnight. The solvent was evaporated, water was added and HCI 1 N until pH=3. The mixture was washed with dichloromethane (2 times). The aqueous phase was basified with NaOH 1 N until pH=11-12 and was extracted with dichloromethane (4 times). The organic phase was dried over Na2SO4, filtered and concentrated to give the title compound as colourless liquid (422 mg, 66%). LC/MS : m/z 189 (M+23)+, Rt: 1.62 min.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/47240; (2009); A1;,
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Application of 61644-18-6, A common heterocyclic compound, 61644-18-6, name is Chloromethyl isobutyrate, molecular formula is C5H9ClO2, 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: Carboxylic acid (±)-9 (5.18 mmol) was dissolved in N,N-dimethylformamide (15.5 mL). Cesium carbonate (4.14 mmol) was added to the solution and the suspension was stirred during 2-3 min after which chloromethyl 2-methylpropanoate (6.73 mmol) was added. After stirring at room temperature during 18-24 h, dichloromethane (30 mL) was added to the mixture and the resulting organic phase was successively washed with water (3×20 mL) and brine (3×20 mL). Organic solvent was eliminated and the residue was submitted to flash chromatography (hexane/ethyl acetate mixtures) to yield the corresponding diester (±)-5.

The synthetic route of 61644-18-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Torres, Susana Y.; Ochoa, Estael; Verdecia, Yamila; Rebolledo, Francisca; Tetrahedron; vol. 70; 31; (2014); p. 4675 – 4684;,
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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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

To a solution of 4-(adamantan-1-yl)phenol(0.8 g, 3.50 mmol) in N,N-dimethylformamide(8 mL) was added anhydrous potassium carbonate(1.45 g, 10.51 mmol) and methyl 2-bromo-2-methylpropanoate(1.15 g, 7.0 mmol), and stirred at room temperature for 12 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give methyl 2-(4-(adamantan-1-yl)phenoxy)-2-methylpropanoate as colorless oil(1.1 g, 94.1% yield). [288] 1H-NMR (MeOH-d4, 500 MHz) delta 7.21 (2H, d, aromatic-H), 6.75 (2H, d, aromatic-H), 3.73 (3H, s, OCH3), 2.05 (3H, brs, adamantyl-H), 1.88 (6H, m, adamantyl-H), 1.77 (6H, m, adamantyl-H), 1.52 (6H, s, (CH3)2).

The synthetic route of 23426-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONGGUK UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; LEE, Kyeong; WON, Mi-Sun; KIM, Hwan-Mook; PARK, Song-Kyu; LEE, Ki-Ho; LEE, Chang-Woo; KIM, Bo-Kyung; BAN, Hyun-Seung; CHUNG, Kyung-Sook; RAVI, Naik; CHOI, Hyun-Kyung; WO2013/48164; (2013); A1;,
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Synthetic Route of 2150-38-1, A common heterocyclic compound, 2150-38-1, name is Methyl 3,4-dimethoxybenzoate, molecular formula is C10H12O4, 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.

(1) Preparation of 3,4-dimethoxybenzoylacetonitrile Dry acetonitrile (1.8 ml) was added to a solution of n-butyllithium (a 2.5M hexane solution, 13.8 ml) in dry THF (30 ml) at -78 C., and the mixture was stirred at the same temperature for 1 hour. To the mixture was added a solution of methyl 3,4-dimethoxybenzoate (6.42 g) in dry THF (15 ml) and the mixture was stirred at -78 C. for 3 hours and then at room temperature for 1 hour. Water (100 ml) was added to the reaction solution which was subsequently extracted with ethyl ether (100 ml). After the aqueous layer was acidified with 6 N hydrochloric acid, it was extracted with ethyl acetate (200 ml*3). The oragnic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. Then, the solvent was distilled away under a reduced pressure. The resultant residue was crystallized from ethyl acetate-hexane to obtain the title compound (3.6 g) as pale yellow crystals. 1H-NMR (CDCl3)delta: 3.95 (3H, s), 3.97 (3H, s), 4.03 (2H, s), 6.92 (1H, d, J=9.0 Hz), 7.49 (1H, d, J=9.0 Hz), 7.51 (1H, s)

The synthetic route of 2150-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; US6180653; (2001); B2;,
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Electric Literature of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, 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 61 120N-(5-(l-piperazinyl)-2-pyridinyl)spiro[cyclopentane-l,9′- pyrido [4′,3′ :3,4] cyclopenta[l,2-d] pyrimidin]-2′-amine 1212-(3-Bromo-4-pyridinyl)-l-cyclopentylethanone (121) Under a nitrogen atmosphere LiHMDS (LOM solution in tetrahydrofuran, 49.6 ml, 49.6 mmol) was added to a solution of methyl cyclopentanecarboxylate (3.630 g, 28.3 mmol) and 3-bromo-4-methylpyridine (2.62 ml, 23.6 mmol) in 10ml of anhydrous THF over a period of 5min at -780C. AfterlOmin the solution was allowed to warm to 2O0C and stirred for 2hours. The solution was then cooled in ice water, before the pH was adjusted to 4.5 with 25% citric acid. After extraction with DCM the organic layer was dried over Na2SO4 and then concentrated to afford 2-(3-bromo-4-pyridinyl)-l-cyclopentylethanone (121) (6.86g, crude). 1H NMR (500 MHz, DMSO-d6) delta 8.68 (IH, s), 8.48 (IH, d, J = 4.9Hz), 7.37 (H, d, J = 4.9 Hz), 4.07 (2H, s), 3.08 (IH, ddd, Jl = 16.1 Hz, J2 = 7.3 Hz, J3 = 1.2 Hz), 1.80- 1.85 (2H, m), 1.72-1.77 (2H, m), 1.55-1.59 (4H, m); LCMS-ESI (POS), M/Z, M+l : Found 268.0

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

Reference:
Patent; AMGEN INC.; WO2009/126584; (2009); A1;,
Ester – Wikipedia,
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Application of 697762-67-7, 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. 697762-67-7, name is Methyl 5-bromo-2-chloro-3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 20 methyl 5-bromo-2-chloro-3-methoxybenzoate (25.0 g, 89.4 mmol) in 13 THF (100 mL), 21 H2O (100 mL) and MeOH (100 mL) was added aq. 5 N 26 NaOH solution dropwise at 0 C. The mixture was stirred at room temperature for 1 hour. 24 conc. HCl was added to the mixture to acidify and the mixture was extracted with EtOAc (500 mL×2). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the 27 title compound (22.6 g, 96%) as an orange solid. 1H NMR (400 MHz, CDCl3) delta 7.55 (s, 1H), 7.13 (s, 1H), 3.89 (s, 3H); [M+H]+ 265.

The synthetic route of Methyl 5-bromo-2-chloro-3-methoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAEWOONG PHARMACEUTICAL CO., LTD.; GREEN CROSS CORPORATION; YOON, Hee-kyoon; PARK, Se-Hwan; YOON, Ji-Sung; CHOI, Soongyu; SEO, Hee Jeong; PARK, Eun-Jung; KONG, Younggyu; SONG, Kwang-Seop; KIM, Min Ju; PARK, So Ok; (55 pag.)US2019/169174; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 884497-46-5, name is Methyl 3-amino-5-fluorobenzoate, 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 884497-46-5, Computed Properties of C8H8FNO2

Step C. Methyl 3-(dibenzylamino)-5-fluorobenzoate. To a solution of methyl 3-amino-5- fluorobenzoate (440 mg, 2.6 mmol) in dry DMF ( 10 mL) was added NaH ( 1 87 mg, 7.8 mmol) portionwise, followed by addition of benzyl bromide (1 . 1 g, 6.5 mmol). The reaction mixture was stirred at 40 C for 16 hr and concentrated. The resulting residue was purified by column chromatography to give the desired product. MS: 350 (M+ l )+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
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