Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 73792-08-2, name is Methyl 4-amino-2-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 73792-08-2, name: Methyl 4-amino-2-fluorobenzoate

Add 2-fluoro-4-aminobenzoic acid methyl ester 2 (3.70 g, 21.8 mmol), cyclobutanone (2.44 g, 34.8 mmol), potassium cyanide (2.12 g, 32.6 mmol) and 37 mL to a 250 mL two-necked flask. Acetic acid, the temperature was raised to 80 C for 12 h, TLC monitoring reaction, (petroleum ether: ethyl acetate = 20:3), after the reaction was completed, 20 mL of water was added to the reaction solution, ethyl acetate extraction (30 ¡Á 3 mL), decompression In addition to the solvent, Compound 3, 5.01 g, brown red solid, yield: 92.5%.

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; Changsha Zeda Pharmaceutical Technology Co., Ltd.; Chen Yongheng; Xu Guangyu; Zhou Wenqiang; (23 pag.)CN108976171; (2018); A;,
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Synthetic Route of 5445-17-0, 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. 5445-17-0 name is Methyl 2-bromopropanoate, 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 22; Preparation of the Compound E-13; Preparation of ethyl 2-methyl-2-(2-methyl-4-(1-(3-(4-methyl-5-oxo-1-(4-trifluoromethyl-phenyl)-4,5-dihydrogen-1H-1,2,4-triazolyl))-benzylthio)-phenoxy)-acetate(E-13); In a 250 ml three-necked flask, to a stirred mixture of lithium aluminum tetrahydride (LiAlH4, 1.0 g, 26.4 mmol) and tetrahydrofuran (THF 30 ml) was added dropwise a solution of 3-methyl-4-hydroxy-phenyl thiocyanic acid (1.38 g, 8.35 mmol) in 20 ml of tetrahydrofuran at 0 C. After 30 min of stirring at 0 C., the mixture was allowed to warm up to room temperature and then stirred for another 2 hours at room temperature. The reaction was quenched by adding ethanol (10 ml). The value of pH of the mixture was adjusted to pH 3-4 by adding 6 N hydrochloric acid in an ice water bath, and then the aqueous phase was extracted with ethyl acetate (3¡Á80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, concentrated under reduced pressure, and purified by column chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.44 g of a disulfide (yellow jelly-like liquid, yield: 62%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy and Mass spectroscopy:1H NMR (400 MHz, CDCl3) delta 2.2 (s, 3H), 5.35 (s, 1H), 6.69 (d, J=8.28 Hz, 1H), 7.18 (dd, J=8.23 Hz, 2.23 Hz, 1H), 7.24 (d, J=2.24 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 15.7, 115.5, 125.0, 128.3, 130.2, 134.0, 154.4; MS (ESI) m/z 278.33 (M+H)+.In 250 ml single-necked flask, to a stirred solution of above crude product (0.7 g, 2.59 mmol) in acetonitrile (60 ml) were added methyl 2-bromo-propionate (0.7 ml, 6.0 mmol) and potassium carbonate (K2CO3, 2 g, 14.5 mmol). The resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (100 ml), and filtrated. The combined solution was evaporated under reduced pressure to give a residue which was purified by chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.0 g of a yellow jelly-like liquid (yield: 86%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, CDCl3) delta 1.63 (d, J=6.84 Hz, 1H); 2.34 (s, 3H), 3.75 (s, 3H), 4.73 (q, J=6.84 Hz, 1H), 6.57-6.61 (m, 1H), 7.19-7.27 (m, 2H).In a 250 ml single-necked flask, to a stirred solution of the above-described product (1.0 g, 2.22 mmol) in ethanol (15 ml) were added 15 ml of water and 5 ml of concentrated hydrochloric acid. Zinc powder (10 g, 153 mmol) was added slowly. After the addition, the reaction mixture was stirred at room temperature for 30 min and then extracted with dichloromethane (3¡Á50 ml). The organic phases were combined, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield a pale-yellow liquid.In a 150 ml single-necked flask, to a stirred solution of the above crude product in 30 ml of acetonitrile were added a solution of 341-bromo-benzyl)-4-methyl-1-(4-trifluoromethyl)phenyl-1H-1,2,4-triazole-5(4H)-one (III-1) (1.8 g, 4.36 mmol) in acetonitrile (30 ml) and potassium carbonate (K2CO3, 2.5 g, 18.1 mmol). The reaction mixture was stirred at room temperature for 6 hours. After the reaction was completed, the reaction mixture was diluted by adding 100 ml of ethyl acetate, filtrated, concentrated under reduced pressure, and subjected to column chromatography (silica-gel H: 300-400 mesh; petroleum ether/ethyl acetate=5:1 v/v) to yield 1.2 g E-13 (a pair of diastereoisomers) (a pale-yellow jelly-like liquid, yield: 50%).Its structure was characterized by the following data from nuclear magnetic resonance spectroscopy:1H NMR (400 MHz, CDCl3) delta 1.61 (d, J=6.84 Hz, 1H); 2.18 (s, 3H), 3.15 (s, 3H), 3.70 (d, J=12.61 Hz, 3H); 4.70 (q, J=6.82 Hz, 1H); 5.18 (s, 1H); 6.51 (d, J=8.46 Hz, 1H), 7.0-7.11 (m, 1H), 7.10-7.15 (m, 1H), 7.34-7.37 (m, 5H), 7.67 (d, J=8.74 Hz, 2H), 8.11 (d, J=8.74 Hz, 2H); 13C NMR (100 MHz, CDCl3) delta 16.1, 18.5, 28.1, 50.6, 52.2, 72.7, 112.1, 118.2, 123.0, 125.5, 126.2, 126.8, 127.1, 128.2, 128.5, 128.9, 133.8, 135.2, 137.7, 140.6, 146.5, 152.6, 156.9, 172.2.

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

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd.; US2011/319458; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2555-28-4, 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. 2555-28-4, name is 7-Methoxy-4-methylcoumarin belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 4-Methyl-6,7-dimethoxycoumarin (0.05 g, 0.227 mmol) was dissolved in acetonitrile (5 ml) in a microwave vessel. N-Bromosuccinimide (0.06 g, 0.340 mmol) was added to the mixture and the vessel inserted into the microwave at 250 W for 5 min at 80 C. The reaction was monitored by thin layer chromatography (silica gel, 3:1 CH2Cl2/EtOAc). Upon completion, the reaction mixture was cooled and the resultant precipitate was collected by vacuum filtration. The crude product was then recrystallized from a mixture of CH2Cl2/MeOH to yield 3-bromo-4-methyl-6,7-dimethoxycoumarin (1a, 0.060 g, 89%)

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, 7-Methoxy-4-methylcoumarin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Marriott, Karla-Sue C.; Bartee, Rena; Morrison, Andrew Z.; Stewart, Leonard; Wesby, Julian; Tetrahedron Letters; vol. 53; 26; (2012); p. 3319 – 3321;,
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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., Recommanded Product: Diethyl fluoromalonate

General procedure: All flasks and stirrer bars were flame dried before use. To the N-oxide (0.2 mmol, 1.0 equiv.), dissolved in 2 cm3 dichloromethane was added Tf2O (0.3 mmol, 1.5 equiv.) at 0 C. In another flask, a suspension of NaH (0.7 mmol, 3.5equiv.) in 1 cm3 tetrahydrofuran was cooled to 0 C and the malonate (0.7 mmol, 3.5 equiv.) was added. After 15 min, the malonate solution was added to the activated N-oxide solution and the mixture was stirred at room temperature for 1 h. The reaction was quenched with NH4Cl solution and the aqueous phase was extracted with dichloromethane. The combined organic layers were washed with brine before being dried over MgSO4. The solvents were removed under reduced pressure and the crude product was purified by column chromatography.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lemmerer, Miran; Teskey, Christopher J.; Kaiser, Daniel; Maulide, Nuno; Monatshefte fur Chemie; vol. 149; 4; (2018); p. 715 – 719;,
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. 35179-98-7, name is Chloromethyl ethyl carbonate, A new synthetic method of this compound is introduced below., Computed Properties of C4H7ClO3

Example 3K (R)-3-{N-(5′-Chloro-2′-fluorobiphenyl-4-ylmethyl)-N’-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic Acid Ethoxycarbonyloxymethyl Ester 2,6-Lutidine (407 mg, 3.8 mmol) was added to a solution of (R)-3-{N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)-N’-[3-(2-fluorophenyl)isoxazole-5-carbonyl]hydrazino}-2-hydroxypropionic acid (200 mg, 380 mmol), carbonic acid chloromethyl ester ethyl ester (105 mg, 760 mumol) and NaI (114 mg, 760 mumol) in DMF (10 mL). The mixture was stirred overnight at room temperature. Water (30 mL) was added and the mixture was extracted with EtOAc (3*40 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by preparative HPLC (MeCN-H2O (0.1% TFA); Gradient 60-70) to yield the title compound as a white solid (56 mg). LC-MS: 630.1 [M+H]+. 1H-NMR: (CD3OD-d4, 400 MHz) delta 1.24 (t, J=5.9 Hz, 3H), 3.30-3.33 (m, 2H), 4.17-4.32 (m, 4H), 4.45 (t, J=4.2 Hz, 1H), 5.78 (br, 2H), 7.20-7.28 (m, 1H), 7.57-7.29 (m, 10H), 7.92-7.95 (m, 1H).

The synthetic route of 35179-98-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hughes, Adam D.; Fleury, Melissa; US2013/330365; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 66315-16-0, A common heterocyclic compound, 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, molecular formula is C9H12N2O2, 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 44: 2-(2,6-Difluoro-phenylamino)-l -methyl- lH-benzoimidazole-5-carboxylic acid 44.1 : 2-(2,6-Difluoro-phenylamin -l-methyl-lH-benzoimidazole-5-carboxylic acid ethyl ester A mixture of 2.00 g (10.3 mmol) 3-amino-4-methylamino-benzoic acid methyl ester and 1.76 g (10.3 mmol) 2,6-difluorophenyl isothiocyanate in 50 mL acetonitrile and 10 mL DMF was stirred at RT for 12 h. 1.80 g (14.3 mmol) Nu,Nu’-diisopropylcarbodiimide was added and the mixture was stirred at 80 C for 5 h. The solvent was removed by distillation. The residue was taken up in EtOAc. The precipitate was filtered off and washed with EtOAc and diethyl ether. The residue was taken up in acetonitrile. The precipitate was filtered off, washed with acetonitrile and diethyl ether and dried. yield: 2.20 g (64 %) ESI-MS: m/z = 332 (M+H)+ Ri(TLC): 0.30 (DCM/MeOH = 19: 1)

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HEIMANN, Annekatrin; DAHMANN, Georg; GRUNDL, Marc; MUELLER, Stephan Georg; WELLENZOHN, Bernd; WO2013/87805; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 6065-82-3, name is Ethyl diethoxyacetate, 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. Quality Control of Ethyl diethoxyacetate

General procedure: A mixture of the appropriate nitrile (4, 2 mmol), hydroxylamine50% (0.132 g, 2 mmol), and a catalytic amount of AcOH was stirredat 150 C for 40 min. After nearly complete conversion to thecorresponding amidoxime, as was indicated by TLC monitoring, theappropriate 2,2-dialkoxyacetate (6, 2 mmol) and K2CO3 (0.276 g,2 mmol) were added to the reaction mixture which was stirred at100 C for further 6 h. After completion of the reaction as indicatedby TLC, the reaction mixture was cooled to room temperature andthe residue was purified by column chromatography using n-hexane-EtOAc (6:1) as eluent. The solvent was removed, and the product was obtained.

The synthetic route of Ethyl diethoxyacetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Adib, Mehdi; Saeedi, Sara; Soheilizad, Mehdi; Bayanati, Maryam; Tajbakhsh, Mahmood; Amanlou, Massoud; Journal of Chemical Research; vol. 40; 5; (2016); p. 314 – 317;,
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Application of 25597-16-4, The chemical industry reduces the impact on the environment during synthesis 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, I believe this compound will play a more active role in future production and life.

Step 5: ethyl 6-bromo-5,7-(dimethyl-D6)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (0.45 g, 1.9 mmol) from step 4, ethyl 4,4,4-trifluorocrotonate (1.3 g, 7.6 mmol) and anhydrous potassium carbonate (2.6 g, 1.9 mmol) were dissolved in DMF (10 mL), and then the system was stirred for 2 hrs at 90 C. At the end of reaction, the reaction system was cooled to room temperature and added with water, the mixture was extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 0.40 g of the product (55%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.88 (s, 1H), 6.76 (s, 1H), 5.7 (m, 1H), 4.3 (dd, 2H), 1.35 (t, 3H) MS (MM-ES+APCI), m/z: 384 (M-H+)

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, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); 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. 27798-60-3, name is Methyl 2-Methoxyphenylacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H12O3

General procedure: A solution of 2.5 M n-BuLi in hexane (1.2 equiv) was added dropwise to a solution of HMDS (1.2 equiv) in anhyd THF at -78 C under argon, and then, after stirring of the mixture for 10 min, a solution of alkyl 2-arylacetate (1 equiv) in THF was added in one portion. The mixture was stirred for 10 min, after which a solution of acyl chloride (1.15 equiv) in THF was added in one portion and the mixture was stirred for 15 min at -78 C and then overnight at r.t. The reaction mixture was quenched with sat. aq NH4Cl, extracted with EtOAc or Et2O, and the organic layer was washed with brine and dried over Na2SO4. The solvents were evaporated to give 3-substituted alkyl 2-aryl-3-oxopropanoate 5, which was used without further purification. NH2OH¡¤HCl (2-5 equiv) was added to a solution of 5 in MeOH and the mixture was refluxed for 24 h. The solvent was evaporated, the residue was treated with H2O, and the precipitate that formed was filtered, washed with H2O and a mixture of PE/EtOAc (10:1), and then dried in air to give pure 3-substituted 4-aryl-5-hydroxyisoxazole/4-arylisoxazol-5(4H)-one 6. The yields of 6 were calculated for the two steps, and is based on the starting alkyl 2-arylacetate.

The synthetic route of 27798-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bodunov, Vladimir A.; Galenko, Ekaterina E.; Galenko, Alexey V.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; Synthesis; vol. 50; 14; (2018); p. 2784 – 2798;,
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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. 394-35-4, name is Methyl 2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7FO2

General procedure: Substituted benzoic acid (1.0 mmol) was dissolved in thionylchloride and refluxed for 2 h, then the solvent was removed underreduced pressure to obtain the white solid. The white solid in methanol was added concentrated sulfuric acid (1 mL) and themixture was refluxed for 4 h, the solvent was removed to obtaincrude solid. The crude solid was extracted with ethyl acetate andwater. The solvents were evaporated to afford the pure product.Finally, the pure product was dissolved in ethanol, and the hydrazinehydrate was added. The mixture was refluxed for 9 h, and thesolvent was removed

The synthetic route of 394-35-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lian, Zhi-Min; Sun, Juan; Zhu, Hai-Liang; Journal of Molecular Structure; vol. 1117; (2016); p. 8 – 16;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics