Month: January 2021

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. 14064-10-9, name is Diethyl 2-chloromalonate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 14064-10-9

A solution of the product of Example 107a (1.2 g, 4.4 mmol) and triethylamine (0.49 g, 4.8 mmol) in dichloromethane (25 ML) was treated dropwise with ethyl chloromalonate (0.73 g, 4.8 mmol), stirred for 2 hr and partitioned between ethyl acetate and water and the layers were separated.The ethyl acetate layer was washed with brine, dried (Na2SO4), and concentrated.The residue was purified by column chromatography on silica gel eluding with hexane and ethyl acetate (3:1) to provide the title compound (1.1 g, 65percent). MS (DCI) m/z 387 (M+H)+.

According to the analysis of related databases, 14064-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pemela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/87577; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 2876-78-0, name is Methyl 1-Naphthaleneacetate, 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. Product Details of 2876-78-0

General procedure: Aryl acetate 1a (2.0 mmol, 1.0 equiv.), CuO (0.2 mmol, 0.1equiv.) and aq TBHP (6.0 mmol, 3.0 equiv.) were added to aflask connected to a reflux condenser. The flask was heated at 110 C for 4.5 h and then cooled to room temperature.Pyridine (0.5 mL, 3.0 equiv.) was added and the mixture washeated to 50 C and stirred for 4.0 h. Thereafter, an aqueoussolution of Na2S2O3 (0.5 mol L-1, 10.0 mL) was added, andthe mixture was extracted with EtOAc (¡Á3). The organiclayers were combined, washed with brine, dried overanhydrous Na2SO4, filtered, concentrated and purified byflash column chromatography over silica gel (200-300 mesh) using petroleum ether/EtOAc (25:1) to afford thedesired compound 2a (172.3 mg, 53% yield) as a colourlessoil.

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

Reference:
Article; Jiang, Jin; Journal of Chemical Research; vol. 48; 7-8; (2019); p. 235 – 240;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 148547-19-7, A common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, 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.

4-Bromo-3-methylbenzylalcohol (4) A solution of methyl 4-bromo-3-methylbenzoate (2.0 g, 8.7 mmol) in dry THF (10 mL) was added to an ice-cooled suspension of lithium aluminiumhydride (400 mg, 10.4 mmol) in dry THF (30 mL). After addition, the mixture was warmed to room temperature and then stirred for 3 h. The excess lithium aluminiumhydride was quenched by successive addition of water (0.4 mL), 15% NaOHaq (0.4 mL), and water (1.2 mL) under ice cooling. The insoluble material appeared was removed by filtration (celite), and the precipitate was washed by AcOEt (20 mL*5). The combined filtrates were washed with brine (50 mL) and then dried over Na2SO4. The solvent was evaporated, and the obtained product (1.6 g, 100%) was used for next step without further purification. 1H-NMR (CDCl3, 400 MHz): delta7.53 (1H, d, J=8.1 Hz), 7.26 (1H, d, J=1.5 Hz), 6.40 (1H, dd, J=8.1, 1.5 Hz), 4.68 (2H, s), 2.44 (3H, s).

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

Reference:
Patent; CHANG, Christopher J.; VAN DE BITTNER, Genevieve V.; HIRAYAMA, Tasuku; CHAN, Jefferson; US2014/51863; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 10602-03-6, name is Ethyl 4-ethynylbenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C11H10O2

General procedure: A solution of 4,5-dibromo-1,2-disubstituted-1H-imidazole 2, 7a-e, or 8a (1 mmol) or 5-alkynyl-4-bromo-1,2-dimethyl-1H-imidazole, alkyne 3 (3 mmol or 1.5 mmol), Pd(MeCN)2Cl2 (10 mg, 0.04 mmol, 4 mol%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26 mg, 0.04 mmol, 4 mol%), and CuI (3 mg, 0.02 mmol, 2 mol%) in DMF (4.5 mL) and DBU (0.5 mL) was stirred at 80 C for 3 h. The reaction mixture was then diluted with EtOAc (100 mL) and sat. aq NH4Cl (100 mL) was added. The resulting mixture was stirred in the open air for 0.5 h and then extracted with EtOAc. The combined organic extractswere washed with H2O (3 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel. This procedure was employed to prepare 1,2-dimethylimidazole-fused enediynes 5a-e, 2-aryl-1-methylimidazole-fused enediynes 9a-d, and 1,2-diarylimidazole-fused enediyne 10a (Table 2).

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:
Article; Lessi, Marco; Panattoni, Alessandro; Guglielmero, Luca; Minei, Pierpaolo; Bellina, Fabio; Synthesis; vol. 51; 4; (2019); p. 933 – 943;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7335-27-5, name is Ethyl 4-chlorobenzoate, 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 7335-27-5, COA of Formula: C9H9ClO2

General procedure: Substituted aromatic acid (0.01 mol) was dissolved in 20 ml absolute ethanol added 1 ml conc. H2SO4 and refluxed for 8 h. The two third volume of reaction mixture was removed under reduced pressure and then poured into crushed ice and neutralized with sodium bicarbonate to obtain esters. In the subsequent step equimolar quantity of substituted ester (0.005 mol) and hydrazine hydrate (0.25 ml, 0.005 mol) in ethanol was refluxed for 24 h with stirring. The two third volume of alcohol was removed under reduced pressure and the reaction mixture was poured into the crushed ice. The resultant precipitate was filtered, washed with water and dried. The solid was recrystallized from 25 ml of 90 % ethanol. The purity of the compounds was checked by TLC using toluene-ethyl acetate-formic acid (5:4:1) as mobile phase.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-chlorobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Ahsan, Mohamed Jawed; Samy, Jeyabalan Govinda; Khalilullah, Habibullah; Nomani, Md. Shivli; Saraswat, Pankaj; Gaur, Ramakant; Singh, Abhimanyu; Bioorganic and Medicinal Chemistry Letters; vol. 21; 24; (2011); p. 7246 – 7250;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 61644-18-6, name is Chloromethyl isobutyrate, 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 61644-18-6, HPLC of Formula: C5H9ClO2

A solution of compound Int-1 (100 mg, 0.239 mmol) in 1.2 mL of acetonitrile, was treated with potassium carbonate (99 mg, 0.717 mmol), potassium iodide (119 mg, 0.717 mmol), 18-crown-6 (3.16 mg, 0.012 mmol) followed by chloromethyl isobutyrate (65.3 mg, 0.478 mmol). The reaction mixture was stirred at 80C for 16 h. The resulting mixture was cooled to room temperature, and partitioned between ethyl acetate and water. The aqueous phase was back extracted with ethyl acetate and the combined organic layers were dried over Na2S04, filtrered, and concentrated in vacuo. The residue was purified on a XBridge1M C18, 30×250 mm column, eluting with acetonitrile / water (5 mM NH4HCO3) at 50 mL / min using a 20 min 20-90% acetonitrile / water gradient. Clean fractions were partitioned between water and (0266) dichloromethane. The organic phase was dried over Na2S04, filtered and concentrated to give compound 14. (0267) Compound 14: 1H MR (500 MHz, DMSO-i4) delta 10.30 (t, J= 5.9 Hz, 1H), 8.55 (s, 1H), 7.40 (td, J= 8.7, 6.6 Hz, 1H), 7.23 (td, J= 10.0, 2.6 Hz, 1H), 7.05 (td, J= 8.6, 2.5 Hz, 1H), 5.84 – 5.61 (m, 2H), 4.63 (dd, J= 14.4, 2.2 Hz, 1H), 4.58 – 4.46 (m, 3H), 3.89 (m, 1H), 3.87 – 3.76 (m, 1H), 3.44 (m, 1H), 2.45 (m, 1H), 2.23 (d, J= 10.2 Hz, 1H), 1.48 – 1.30 (m, 3H), 1.11 (s, 3H), 1.04 (d, J= 7.0 Hz, 6H). LCMS M+l = 519.3.

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; MERCK SHARP & DOHME CORP.; YU, Tao; MCCAULEY, John, A.; WHITEHEAD, Alan; APGAR, James, M.; RAHEEM, Izzat, T.; DONG, Guizhen; WADDELL, Sherman, T.; LI, Hong; (43 pag.)WO2018/140368; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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.

Reference Example 6; Ethyl 3-methyl-2-(5-phenyl-1,1-dioxothieno[2,3-d]isothiazol-2(3H)-yl)butyrate; The compound of Reference Example 5 (67 mg) and sodium hydride (13 mg, Wako Pure Chemical Industries, Ltd., containing 40% mineral oil) were dissolved in N,N-dimethylformamide (1 ml), and the resultant solution was stirred at 60 C. for 1 hour. Then, ethyl 2-bromoisovalerate (68 mul, manufactured by Wako Pure Chemical Industries, Ltd.) was added thereto and the reaction solution was further stirred for 24 hours. The reaction mixture was stood to cool to room temperature and then concentrated, and ethyl acetate (2 ml) and water (2 ml) were added thereto. A product was extracted with ethyl acetate, washed with saturated saline, dried with magnesium sulfate and then concentrated. The obtained residue was put into a silica gel column (hexane:ethyl acetate=5:1) to give 16 mg of the titled compound. LC-MS: HPLC retention time 4.94 minutes (LC Condition 2), m/z 380 (MH+)

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-bromo-3-methylbutanoate, its application will become more common.

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/192154; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 148547-19-7

2l2′-dimethyl-1 l1 ‘-biphenyl-4-carboxylic acidStep 1: methyl 2,2′-dimethyl-1, 1’-biphenyl-4-carboxylate To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15 g, 65 mmol) in toluene (200 mL) and water (200 mL), was added o-tolylboronic acid (10.68 g, 78 mmol) followed by potassium carbonate (45.25 g, 32.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 120 C for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-d6, 400 MHz) delta 7.91 (s, 1 H), 7.83-7.81 (m, 1 H), 7.33-7.30 (m, 2H), 7.28-7.26 (m, 1 H), 7.25-7.22 (m, 1 H), 7.07-7.05 (m, 1 H), 3.86-3.81 (s, 3H), 2.09-2 (s, 3H), 1.97-1.92 (s, 3H). HPLC (Method B), Rt: 3.01 min (purity: 98.71 %).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 148547-19-7.

Reference:
Patent; MERCK SERONO S.A.; MUZERELLE, Mathilde; QUATTROPANI, Anna; MONTAGNE, Cyril; DORBAIS, Jerome; WO2010/69949; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1559-02-0, 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 1559-02-0 as follows.

In the 2L three-mouth reaction bottle,Add 255.3 g of diethyl 1,1-cyclopropanedicarboxylate,840mL EtOH,The ice water bath cools it to 0 C.Slowly add 137.32g KHCO3The temperature control is added below 30 C.Naturally rise to room temperature,Stir the reaction for 15 h,TLC monitors the reaction completely,Add 1L of water,Extracted with (PE: EA = 1:1) 300 mL ¡Á 2,Remove the organic phase,Concentrated HCl adjusts pH=2,Extracted with EA 370mL¡Á2,Take the organic phase,Desolvent1,1-cyclopropanedicarboxylic acid monoethyl ester 201.7 g,The yield was 93%.

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan Institute of Technology; Huang Qimao; Feng Jinjin; Gao Hui; (13 pag.)CN105111155; (2018); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 55666-43-8,Some common heterocyclic compound, 55666-43-8, name is tert-Butyl 3-bromopropanoate, molecular formula is C7H13BrO2, 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 suspension of [2- (4-METHYLSULFANYL-PHENYLSULFANYL) ETHYLAMINE HYDROCHLORIDE] salt (0.63 g, 2.69 [MMOLS)] in anhydrous tetrahydrofuran (20 ml) was added triethylamine (0.78 ml, 5.64 mmols) at [0C] under nitrogen. The mixture was stirred for 30 mins. To this was added dropwise a solution of [TERT-BUTYL] bromo acetate (0.42 [ML,] 2.82 [MMOLS)] in anhydrous tetrahydrofuran (10 [ML).] The mixture was warmed to room temperature and stirred fro 18 hours. The solvent was removed under reduced pressure and the residue partitioned between water (50 ml) and diethyl ether (30 [ML).] The aqueous was extracted with diethyl ether (2 x 30 [ML),] the combined organics dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a solvent gradient of heptane: ethyl acetate (1: 1) to give the title compound (0.25 g, 29 %) as a colourless oil. [‘H-NMR] (400 MHz, CD30D) : [A] = 1.44 (s, 9H), 2.45 (s, 3H), 2.75 (t, 2H), 3.01 (t, 2H), 3.20 (brs, 2H), 7.20 (d, 2H), 7.33 (d, 2H). LRMS [(ELECTROSPRAY)] : m/z [M + [H] + 314.] Microanalysis : Found: C, 57.28 ; H, 7.38 ; N, 4.41. [C15H23NO2S2] requires C, 57.47 ; H, 7.39 ; N, 4.47%.

The synthetic route of 55666-43-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/16583; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics