Month: March 2021

These common heterocyclic compound, 5445-17-0, name is Methyl 2-bromopropanoate, 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 C4H7BrO2

Add p-chlorodiphenyl disulfide (0.5 mmol) to a 10 mL reaction tube.Methyl alpha-bromopropionate (1.0 mmol),Zinc powder (2.0 mmol) solvent toluene (2 mL) and dinuclear Schiff base titanium perfluorooctanesulfonic acid complex (X=OSO2C8F17)(0.04 mmol), stirred for 4 h at 25C. Spin dry after the reaction is over.The residue was extracted with ether three times and the filtrate was evaporatedThe crude product was separated by silica gel column chromatography.This gave methyl 2-p-chlorophenylthiopropionate as a colorless oily liquid in a yield of 86%.

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

Reference:
Patent; Shanxi Medical University; Li Ningbo; Wang Lingxiao; Wang Haojiang; Zhao Wenjie; (13 pag.)CN107722049; (2018); A;,
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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. 618-89-3, name is Methyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 3-bromobenzoate

I. Methyl 3-benzylbenzoate; [00306] A solution of 3-bromomethylbenzoate (500 mg, 2.18 mmol), phenylboronic acid (290 mg, 2.40 mmol), PdCl2(PPh3)2 (46 mg, 0.07 mmol) and K3PO4 (1.16 g, 5.45 mmol) in DMF (10 mL) and water (2 mL) was heated at 8O0C for 1 hr and then cooled to room temperature and diluted with EtOAc. The reaction mixture was washed with water (3 times) and saturated NaCl, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with 1 :19 EtOAc:hexanes to give a colorless oil (353 mg, 72%).

The synthetic route of 618-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ENCYSIVE PHARMACEUTICALS, INC.; WO2008/79371; (2008); 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 59247-47-1 as follows. Product Details of 59247-47-1

To a solution of tert-butyl 4-bromobenzoate (2 g, 7.8 mmol) and 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (4 g, 16 mmol) in 1,4-dioxane (30 mL) was added 1,1?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane (0.64 g, 0.8 mmol) and potassium acetate (3.0 g, 31 mmol). The reaction mixture was stirred at 90¡ã C. under nitrogen for 12 hours. After the reaction, it was allowed to cool to room temperature and concentrated in vacuo, then diluted with ethyl acetate (100 mL), washed with water (100 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.8 g, 75percent). 1H NMR (300 MHz, CDCl3): delta 7.95 (d, J=8.1 Hz, 2H), 7.83 (d, J=8.4 Hz, 2H), 1.59 (s, 9H), 1.35 (s, 12H).

According to the analysis of related databases, 59247-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
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Related Products of 711-01-3, 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 711-01-3 as follows.

General procedure: 1 equiv. substrate, 2 equiv. TsCN, 1 equiv CAN, 1 equiv Li2CO3, 0.2 equiv. NHPI and 5 mL DCE were stirred for 16 h at 75 ¡ãC. After 6 h 0.2 equiv. NHPI were added. The reactions mixture was allowed to cool down to room temperature andfiltered over silica gel (50 mL EtOAc, 50 mL MeCN, 50 mL EtOAc).

According to the analysis of related databases, 711-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Berndt, Jan-Philipp; Erb, Frederik R.; Ochmann, Lukas; Beppler, Jaqueline; Schreiner, Peter R.; Synlett; vol. 30; 4; (2019); p. 493 – 498;,
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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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H6F2O2

Intermediate 15 (2.57 g, 0.0101 mol) was stirred in toluene (150 mL) at 0C under N2. Potasssium tert.-butoxide (1.59 g, 14.2 mmol) was added at 0-5C, ethyldifluoroacetate (1.52 g, 0.0122 mol) was added dropwise at 0-5C. RM was stirred at RT for 2 h. The RM was washed with 10%> H2SO4 in water and the OL was dried on MgS04, filtered and evaporated to yield intermediate 16 (3.34 g, 99%).

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; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; TRESADERN, Gary; JACOBY, Edgar; OEHLRICH, Daniel; GIJSEN, Henricus, Jacobus, Maria; (67 pag.)WO2018/83103; (2018); A1;,
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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. 87-24-1, name is Ethyl 2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H12O2

Example 1 Preparation of intermediate A: Ethyl 2-methylbenzoate (15.0 g, 91 mmol) in ethyl acetate (400 mL) was treated with N-bromosuccinimide (19.5 g, 110 mmol). The resulting solution was illuminated with a 65 W mercury-halogen lamp for 16 h, which provided enough heat to bring the solution to a gentle reflux. The reaction mixture was cooled to room temperature, and ethyl acetate and water were added (100 mL each). After separation of the organic layer, the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic extracts were washed twice with water (100 mL each) and then with brine (100 mL), and then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product so obtained was purified by flash chromatography (ethyl acetate/hexane) to afford A as a yellow oil (21.3 g).

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 87-24-1.

Reference:
Patent; Roche Palo Alto LLC; US2010/16312; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 70347-04-5, 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. 70347-04-5, name is Methyl 4-methoxy-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 4-methoxy-3-methylbenzoate (16 g) was dissolved in EtOAc (100 mL) and then N- bromosuccinimide (18.96 g) and 2,2′-azobisisobutyronitrile (1 g) were added. The mixture was then heated to 800C for 4 h. After cooling to r.t. sat. sodium thiosulfate solution was added, the organic phase was separated, washed with brine, dried and the solvents removed by evaporation. The crude product was dissolved in mixture of isohexane-EtOAc (9:1) and a solid was produced which was collected to give the subtitle compound (11.82 g); 1H NMR (CDCl3): 8.05-7.98 (m, 2H), 6.91 (d, IH), 4.55 (s, 2H), 3.96 (s, 3H), 3.89 (s, 3H). LC-MS m/z 260.

The synthetic route of Methyl 4-methoxy-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; DAINIPPON SUMITOMO PHARMA CO., LTD; ASTRAZENECA UK LIMITED; BENNETT, Nicholas, James; MCINALLY, Thomas; THOM, Stephen; WO2010/133885; (2010); A1;,
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Some common heterocyclic compound, 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, molecular formula is C4H5ClF2O2, 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. category: esters-buliding-blocks

TEOF (130 g, 0.88 mol) was placed in a flask equipped with a magnetic stirring bar and a vacuum distillation cooler. ECDFAA (35 g, 0.175 mol) was added. The resulting mixture was heated to 110C (outer temperature of the flask) under a mild vacuum (300 mbar) ; ethanol formed during the reaction is slowly distilled out of the vessel. After 2h, the starting material was completely consumed, and product formation was observed by GC analysis. Excess of TEOF was removed from the reaction mixture by distillation (at 100C, starting with a pressure of 100 mbar at the beginning and 10 mbar at the end, to remove all TEOF traces), resulting pure product as pale yellow liquid with quantitative yield. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 1.15 (t, 3 H) 1.20 (t, 3 H) 1.27 (t, 3 H) 3.49 – 3.57 (m, 1H) 3.61 – 3.69 (m, 1H) 3.71 – 3.79 (m, 2 H) 4.23 (q, 2 H) 4.34 (d, J=8.24 Hz, 1 H) 5.18 (d, J=8.24 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 383-62-0, its application will become more common.

Reference:
Patent; SOLVAY SA; Januzems, Janis; EP2644598; (2013); A1;,
Ester – Wikipedia,
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Electric Literature of 18595-14-7, 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. 18595-14-7 name is Methyl 4-amino-3-methylbenzoate, 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.

Under a nitrogen atmosphere, to a 100-mL four-necked flask were added 5-methylmenthyl carboxylic acid (rac-11a) (600 mg, 3.03 mmol) obtained in Synthesis Example 7, 8, 9, or 19, thionyl chloride (0.33 mL, 1.50 eq.), and a catalytic amount of DMF, followed by stirring at room temperature for 3 hours. The solution in the system was distilled off under reduced pressure, and toluene (2 mL) was added thereto. The inside of the system was cooled to 10 C. or lower in an ice bath, and 3-methyl-4-aminobenzoic acid methyl ester (1.50 g, 3.0 eq.) was added slowly thereto. After two and a half hours, completion of the reaction was confirmed by GC-MS, and a post-treatment was performed. The reaction solution was transferred to a separating funnel, and tap water and chloroform were added thereto to effect washing. The oil layer was washed twice with dilute hydrochloric acid, and further washed once with a saturated saline solution, and then dried with anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and then isolation and purification were performed by column chromatography (heptane/ethyl acetate=4/1), whereby an amorphous solid was obtained (306 mg, yield: 29%). HRMS: mass: 345.2304 actual measurement value: 345.2298 1H-NMR (500 MHz, CDCl3): delta0.85-0.98 (m, 12H), 1.20-1.33 (m, 3H), 1.45-1.65 (m, 4H), 1.82 (quid, 1H, J=6.6, 2.1 Hz), 2.29-2.40 (m, 4H), 7.05 (br, 1H), 7.86-7.90 (m, 2H), 8.14 (d, 1H, J=8.2 Hz)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; TAKASAGO INTERNATIONAL CORPORATION; ITOH, Hisanori; HORI, Yoji; OTSUKA, Masashi; MATSUMOTO, Takaji; SATO, Tomoharu; (50 pag.)US2018/57447; (2018); A1;,
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Electric Literature of 91367-05-4, 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. 91367-05-4 name is Methyl 4-chloro-3-methylbenzoate, 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.

17.0 mL glacial acetic acid, 16.5 mL acetic anhydride and 2.5 mL H2SO4 were cooled in ice bath. Then X13 1.84 g (0.01 mol) and Cr2O3 3 g (0.03 mol) were added in small portion. The mixture was reacted in ice bath for 3 h. The reaction solution was poured into 200.0 mL ice water and stirred vigorously for 30 min. The resulting precipitates were collected by filtration and washed with water (70.0 mL x 3) to afford gray solid which was added into 50.0 mL eggplant flask. 16.0 mL CH3OH, 16.0 mL water and 0.4 mL H2SO4 were added to and refluxed for 30 min. The residue was added into water,and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined ethyl acetate extracts were washed with water (80 mL) and brine (80 mL) respectively, and then dried with anhydrous Na2SO4. When the solvent was evaporated, the yield of yellow solid compound X14 was 1.35 g (68.2 %). mp: 131-133 C. 1H NMR (300 MHz, DMSO-d6): delta 3.90 (s, 3H, OCH3), 7.79 (d, 1H, Ar-H, J = 8.4 Hz), 8.18 (d, 1H, Ar-H, J = 8.4 Hz), 8.35 (s, 1H, Ar-H), 10.34 (s, 1H, CHO). IR (KBr): 3425, 3082, 3003, 2953, 1726, 1720, 1689, 1188, 983, 759 cm-1. MS [M+H]+: 199.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-chloro-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Article; Jiao, Yu; Xin, Bo-Tao; Zhang, Yanmin; Wu, Jianbing; Lu, Xiaolin; Zheng, Ying; Tang, Weifang; Zhou, Xiang; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 170 – 183;,
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