Category: esters-buliding-blocks

Electric Literature of 57486-67-6, A common heterocyclic compound, 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, molecular formula is C9H9FO2, 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-tert-butyl 4-methyl 4-(2-fluorophenyl)piperidine-1,4-dicarboxylate. A flask was charged with sodium hydride (2.14 g, 89.2 mmol) and dimethylformamide (70 ml) at 0 C. under nitrogen. Methyl 2-(2-fluorophenyl)acetate (5 g, 29.7 mmol) was added to the flask, and after stirring for 25 min, tert-butyl bis(2-chloroethyl)carbamate (8.6 g, 35.6 mmol) was added. The reaction was allowed to warm to rt and stirred overnight. The reaction was quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate (5¡Á100 mL). The organics were collected, washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified via silica gel chromatography (10/90?50/50 ethyl acetate/hexanes) to yield 1.7 g (17%) of the desired product. 1H-NMR (CDCl3, 400 MHz) delta ppm 7.29 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 7.00 (m, 1H), 3.86 (m, 2H), 3.67 (m, 3H), 3.22 (m, 2H), 2.37 (m, 2H), 1.96 (m, 2H), 1.44 (s, 9H). Mass spec.: 360.22 (MNa)+. LC tr=3.503 min (Phenomenex-Luna 4.6¡Á50 mm S10, 10% MeOH/90% H2O/0.1% TFA?90% MeOH/10% H2O/0.1% TFA Gradient Time=4 min, Flow rate=4 mL/min)

The synthetic route of 57486-67-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/249607; (2007); A1;,
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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 2905-67-1 as follows. Computed Properties of C8H6Cl2O2

Methyl 3,5-dichlorobenzoate (2-D) (1.07 g, 5.0 mmol) was suspended in a vigorously stirring solution of methylamine (40%/H20, 5.0 mL). After heating gently for 10 min, the mixture was stirred at room temperature for 18 h. The mixture was extracted with methylene chloride and the extract dried (MgS04) to provide 3,5-dichloro-N-methylbenzamide (2-E).

According to the analysis of related databases, 2905-67-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2005/97759; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 103-26-4, 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. 103-26-4, name is Methyl cinnamate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.28 ml, 1.85 mmol, 3.0 eq) wasadded to a solution of (E)-3-Phenyl-acrylic acid methyl ester (100 mg, 0.62mmol, 1.0 eq) in methanol (0.35 mL). The resulting solution was stirred at roomtemperature and hydroxylamine in aqueous solution 50% (0.38 ml, 6.17 mmol, 10.0eq) was added. After 30 minutes the reaction was stopped and purified bypreparative HPLC to afford (E)-N-Hydroxy-3-phenyl-acrylamide(92 mg, 0.56 mmol, 91%) as an off-whitesolid: MS ES+ m/z 164.35(M+H)+; 1H NMR (400 MHz, DMSO-d6) delta 10.67 (s, 1H), 7.56 (d, J = 7.2 Hz, 2H), 7.48(d, J = 15.8 Hz, 1H), 7.44 – 7.30 (m, 3H), 6.51 (d, J = 15.8 Hz,1H) ; 13C NMR (101 MHz, DMSO-d6) delta 163.0, 138.6, 135.0, 129.7, 129.1, 127.7, 119.

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 cinnamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Beillard, Audrey; Bhurruth-Alcor, Yushma; Bouix-Peter, Claire; Bouquet, Karinne; Chambon, Sandrine; Clary, Laurence; Harris, Craig S.; Millois, Corinne; Mouis, Gregoire; Ouvry, Gilles; Pierre, Romain; Reitz, Arnaud; Tomas, Loic; Tetrahedron Letters; vol. 57; 20; (2016); p. 2165 – 2170;,
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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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 55666-43-8

Intermediate 35: tert-butyl 3-f7-famino(hvdroxyimino)methvn-3,4-dihydroisoquinolin- 2(1 hP-ylipropanoateStep 1 : tert-butyl 3-(7-cyano-3,4-dihydroisoquinolin-2(1 H)-yl)propanoate; 7-Cyano-1 ,2,3,4-tetrahydroisoquinoline (7 g; 44.25 mmol; 1 eq.) and K2CO3 (7.34 g; 53.1 mmol; 1.2 eq) were suspended in CH3CN (280 ml_). te/f-Butyl 3-bromopropionate (7.77 ml 46.46 mmol; 1.05 eq.) was added. The reaction mixture was heated to 700C for 24 hours. As the reaction was not complete, tert-butyl 3-bromopropionate (3.70 ml 22.12 mmol; 0.50 eq.) and K2CO3 (3.06 g; 22.12 mmol; 0.5 eq) were added and the mixture was stirred at 70 0C for additional 48 hours. Solvents were removed under vacuum and the solid residue was partitioned between NaHCO3 sat (100 ml.) and EtOAc (200 ml_). The organic layer was then washed with brine and dried over magnesium to give the title compound as a yellow oil (1 1.9 g; 93.9 %). It was used in the next step without further purification. 1H NMR: (DMSO-dbeta, 400MHz) delta 7.57-7.54 (m, 2H), 7.32-7.29 (m, 1 H), 3.59 (s, 2H), 2.87-2.83 (t, J = 5.94 Hz, 2H), 2.74-2.66 (m, 4H), 2.46-2.42 (t, J = 7.01 Hz, 2H), 1.39 (s, 9H). UPLC/MS: 287.1 (M+H)+. HPLC (Method A) Rt 2.37 min (Purity: 96.4 %).

According to the analysis of related databases, 55666-43-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (2010); 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. 4341-76-8, name is Ethyl 2-butynoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step A: (Z)-methyl pent-2-enoate To a mixture of ethyl but-2-ynoate (50 g, 446 mmol) and Lindlar catalyst (9.49 g, 4.46 mmol) in 1 L round-bottom flask THF (1013 mL) and pyridine (101 mL) were added. The reaction mixture was degassed and purged with nitrogen (5*). The reaction was then blanked with a hydrogen balloon. After about 48 h the suspension was filtered through a pad of Celite washing with THF (3*100 mL). The THF was removed in vacuo at about 40 C. and 200 mbar. The residue was diluted with Et2O (1 L) and washed with water (3*200 mL) followed by 20% CuSO4 aqueous solution (5*200 mL) followed by water (3*150 mL) and dried over MgSO4, filtered and the solvent was removed in vacuo at about 40 C. and 200 mbar to give (Z)-methyl pent-2-enoate (45.3 g, 89%) as an oil. 1H NMR (400 MHz, CDCl3) delta 6.34-6.30 (m, 1H), 5.82-5.75 (m, 1H), 4.20-4.14 (m, 2H), 2.14 (dd, 3H), 1.31-1.27 (m, 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; ABBVIE INC.; Wishart, Neil; Bonafoux, Dominique F.; Frank, Kristine E.; Hobson, Adrian D.; Konopacki, Donald B.; Martinez, Gloria Y.; Wang, Lu; US2013/72470; (2013); A1;,
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Ester – an overview | ScienceDirect Topics

Electric Literature of 13831-03-3, A common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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 suspension of copper(I) iodide (335 mg) in tetrahydrofuran (100 mL) was added t-butyl prpiolate (3.63 mL), diisopropylethylamine (4.62 mL) and a solution of 5(R)-azidomethyl-3-[4-(1-cyanocyclopropan-1-yl)phenyl]oxazolidin-2-one (5.00 g) in tetrahydrofuran (10 mL), the mixture was stirred at room temperature for 2.5 hours, and then concentrated in vacuo. After dilution of the residue with ethyl acetate, the resulting precipitates were filtered off, and then concentrated in vacuo. Treatment of the residue with ethyl acetate gave t-butyl 1-[5(R)-3-[4-(1-cyanocyclopropan-1-yl)phenyl]-2-oxooxazolidin-5-ylmethyl]-1,2,3-triazole-4-carboxylate (6.85 g). [0423] MS (EI+) m/z: 409 (M+). [0424] HRMS (EI+) for C21H23N5O4 (M+): calcd, 409.1750; found, 409.1729.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Yasumichi; US2003/225107; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 2905-67-1, 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 2905-67-1 as follows.

Step A: Preparation of 1 -(3,5 -dichlorophenyl)-3 -(2-fluorophenyl)- 1,3 -propanedioneTo a solution of tetrahydrofuran (20 mL) and sodium hydride (60% dispersion in mineral oil, 0.35 g, 8.7 mmol) was added 2?-fluoroacetophenone (0.59 mL, 4.9 mmol), followed by 3,5-dichlorobenzoic acid methyl ester (1.0 g, 4.9 mmol). The mixture was heated at reflux for 24 h. After cooling to ambient temperature, 1 N aqueous hydrochloricacid was added, and the mixture was extracted three times with dichloromethane. The extracts were combined, dried with Mg504 and filtered. The filtrate was concentrated to give a tan solid (1.8 g), which was used without further purification.

According to the analysis of related databases, 2905-67-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; SELBY, Thomas Paul; TRAVIS, David Andrew; DEPREZ, Nicholas Ryan; SATTERFIELD, Andrew Duncan; WO2015/167795; (2015); A1;,
Ester – Wikipedia,
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Synthetic Route of 135484-83-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 135484-83-2 name is Methyl 2-amino-4-bromobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 16a4-Bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-benzoic acid methyl ester2-Amino-4-bromo-benzoic acid methyl ester (1.2g, 5.0 mmol) was combined with2,4,5-trichloro-pyrimidine (5.33 mL, 46.5 mmol) and EtN(i-Pr)2 (0.95 mL, 5.5 mmol), and the mixture was warmed to 120C. After 16 hours the excess 2,4,5-trichloro-pyrimidine was removed under high vacuum, and the residue was then treated with 1 : 1 MeOH: water. The resulting solid was filtered, retriturated with 1 : 1 MeOH: water, re filtered, and the resulting solid triturated in MeOH at 50C. After filtering, the solid was rinsed liberally with MeOH. After air drying 4-Bromo-2-(2,5-dichloro-pyrimidin-4-ylamino)-benzoic acid methyl ester was recovered in 52% yield as a brown solid and was carried on for subsequent steps without further manipulation. LC/MS: M+H= 377.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-amino-4-bromobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; CEPHALON, INC.; BRESLIN, Henry J.; DORSEY, Bruce; OTT, Gregory R.; WO2012/125603; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 121-98-2, name is Methyl 4-methoxybenzoate, 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 121-98-2, Formula: C9H10O3

Methyl-4-methoxybenzoate (i) was refluxed with 5 mL of hydrazine hydrate solution in 15 mL of methanol for 6 h. The excess hydrazine and methanol was then removed in vacuo to obtain crude product which was then recrystallized from methanol to afford pure 4-methoxybenzohydrazide in 92% yield. Pure 4-methoxybenzohydrazide(20 mmol, 3.32 g) were refluxed with Lawesson’s reagent (20 mmol,8.09 g) of in dry toluene for 8 h to get corresponding 4-methoxybenzothiohydrazide. The crude product was washed with diethyl ether and crystallized from methanol to get pure 4-methoxybenzothiohydrazide in 91% yield. In order to get thiadiazole derivatives 1-25, a mixture of 4-methoxybenzothiohydrazide (0.5 mmol) and the corresponding aromatic aldehyde (0.5 mmol) were taken together in around-bottomed flask and was then added drop wise POCl3 (5 mL) carefully. The reaction mixture was heated to reflux for 4-6 h, then cooled to room temperature and poured onto crushed ice. NaHCO3 solution was added and the resulting solid mass precipitated out was filtered, dried, and crystallized from methanol in good to excellent yields.

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

Reference:
Article; Taha, Muhammad; Barak Almandil, Noor; Rashid, Umer; Ali, Muhammad; Ibrahim, Mohamed; Gollapalli, Mohammed; Mosaddik, Ashik; Mohammed Khan, Khalid; Bioorganic Chemistry; vol. 91; (2019);,
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Ester – an overview | ScienceDirect Topics

Reference of 685892-23-3, 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. 685892-23-3, name is Methyl 2-bromo-6-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Step 1. Preparation of methyl 2-chloro-6-cvclopropylbenzoate (i-la) [00137] Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P ( 224 mg, 0.8 mmol) and K3PO4 (2.5 g, 12.0 mmol) were mixed in toluene (20 mL) and H2O (2.5 mL). The mixture was stirred at 100C for 14h under N2 atmosphere. The mixture was cooled down and poured into water. The mixture was extracted with EtOAc and the organic layer was dried over Na2SC>4 and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc 15/1) to give the title compound. MS: 211 (M+l).

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-6-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LAPOINTE, Blair, T.; FULLER, Peter, H.; GUNAYDIN, Hakan; LIU, Kun; SCOTT, Mark, E.; TROTTER, B., Wesley; ZHANG, Hongjun; (211 pag.)WO2017/75182; (2017); A1;,
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Ester – an overview | ScienceDirect Topics