Tag: M.W=100-200

Electric Literature of 210530-71-5, 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 210530-71-5 as follows.

To a stirred mixture of methyl 2- (3, 4-difluorophenyl) acetate (4.5 g, crude) in CCl4 (50 mL) was added NBS (6.0 g, 33.7 mmol) and HBr/HOAc (1.0 mL) . After the addition, the reaction mixture was stirred for 3 hours at 85. The solid of the reaction was filter out, the filtrate was concentrated, and this residue was dissolved by H2O (50 mL) , extracted with EtOAc (50 mL x 3) , The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give methyl 2-bromo-2- (3, 4-difluorophenyl) acetate (4.0 g, crud) as a yellow oil. MS: M/e 266 (M+1)+

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); 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 2967-93-3 as follows. Formula: C9H9FO2

Step 2; Preparation of 2-Fluoro-5-formyl-benzoic acid methyl ester; Add Af-bromosuccinimide (2.46 g, 13.86 mmol) and benzoyl peroxide (0.152 g, 0.630mmol) to a solution of 2-fluoro-5-methyl-benzoic acid methyl ester (1.06 g, 6.30 mmol)in carbon tetrachloride (50 mL). Heat the mixture at reflux for 4 h. Cool the mixture toroom temperature and wash with saturated aqueous sodium bicarbonate solution (10 mL)and brine (10 mL). Dry the organic layer over anhydrous sodium sulfate, filter, andconcentrate under reduced pressure. Dissolve the resulting residue in dimethylsulfoxide(30 mL) and heat at reflux for 16 h. Cool the mixture to room temperature and dilutewith water (100 mL) and ethyl acetate (100 mL). Extract the aqueous layer with ethylacetate (3 x 100 mL). Wash the combined organic layers with water (3 x 100 mL),followed by brine (100 mL). Dry the organic layer over anhydrous sodium sulfate, filterand concentrate. Purify the residue by chromatography over silica gel, eluting withhexanes/ethyl acetate (80:20), to provide the title compound as a tan solid (0.228 g, 20%).

According to the analysis of related databases, 2967-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/2342; (2006); A1;,
Ester – Wikipedia,
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Reference of 25415-67-2, 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. 25415-67-2, name is Ethyl 4-methylpentanoate, This compound has unique chemical properties. The synthetic route is as follows.

Tetrahydrofuran (35 ml) was cooled down to -70C under inert gas atmosphere. At this temperature, 4.44 ml (11.1 mmol) of n-butyllithium solution (2.5 M in hexanes) and then 0.51 ml (9.71 mmol) acetonitrile were added dropwise. After 3 min at -70C, 1 .1 5 ml (6.93 mmol) ethyl 4- methylpentanoate were added dropwise at such a rate that the temperature of the solution did not exceed -66C. The mixture was stirred for 2 h at -45C before 22.2 ml of 1 N hydrochloric acid were added dropwise. The reaction mixture was concentrated under reduced pressure, and the residue was mixed with diethyl ether. After filtration through silica gel, the filtrate was evaporated under reduced pressure to yield 1.05 g of the crude title compound, which was used in the next step without further purification.GC-MS (method 5): Rt = 3.23 min; MS (EIpos): m/z = 138 (M-H)+ ‘H-NMR (DMSO-dg): delta = 4.03 (s, 2H), 2.51 (t, 2H), 1.50 (sext, 1H), 1.38 (q, 2H), 1.35 (d, 6H) ppm.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-methylpentanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Schering Pharma AG; MICHELS, Martin; FOLLMANN, Markus; VAKALOPOULOS, Alexandros; ZIMMERMANN, Katja; TEUSCH, Nicole; LOBELL, Mario; ENGEL, Karen; WO2011/42367; (2011); A1;,
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Electric Literature of 2459-25-8, The chemical industry reduces the impact on the environment during synthesis 2459-25-8, name is Methyl 2-naphthoate, I believe this compound will play a more active role in future production and life.

4a (1.54 g, 9 mmol) was dissolved in 30 ml of ethanol, hydrazine hydrate was added, and the reaction was refluxed overnight. The next day, TLC monitored the reaction completely. At room temperature, a yellow solid precipitated continuously. Concentrate to a small volume, ice bath for 30 minutes, and filter to obtain a solid. Drying gave 1.21 g of a yellow solid. Yield: 72%.

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 2-naphthoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University; Chen Jianzhong; Yang Bo; He Qiaojun; Pan Youlu; Ying Meidan; (29 pag.)CN108329232; (2018); A;,
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Application of 39552-81-3, 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. 39552-81-3, name is Methyl 2-(4-aminophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 100 9-Bromo-5-(p-methoxycarbonylmethylphenylcarbamoylmethyl)-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione A procedure similar to that described in Example 52 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (340 mg, 1 mmol) and p-methoxycarbonylmethylaniline (215 mg, 1.3 mmol) to give 395 mg of the title compound (81%): mp 262 C. (dec); 1 H NMR (270 MHz, DMSO-d6) delta10.02 (s, 1H), 7.50 (d, 2H, J=8.3 Hz), 7.23 (bs, 1H), 7.18 (d, 2H, J=8.3 Hz), 7.17 (bs, 1H), 5.17~5.26 (m, 1H), 3.61~3.62 (m, 5H), 3.06 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.84 (dm, 1H, J=17.1 Hz),2.56~2.66 (m, 2H), 2.11 (dm, 1H, J=13.5 Hz), 1.76~1.94 (m, 1H).

The synthetic route of Methyl 2-(4-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; US5616586; (1997); A;,
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Some common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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 tert-Butyl cyclopropanecarboxylate

Example 25ATert-Butyl 1-(prop-2-en-1-yl)cyclopropanecarboxylate 9.9 ml (70.32 mmol) of diisopropylamine were initially charged in 35 ml of THF, 28.1 ml (70.32 mmol) of a 2.5 M solution of n-butyllithium in n-hexane were added at -40 C. and the mixture was stirred for 30 min. The reaction mixture was then cooled to -78 C., and a solution of 10 g (70.32 mmol) of tert-butyl cyclopropanecarboxylate in 5 ml of THF was added dropwise. The mixture was stirred at -78 C. for 4 h, and a solution of 5.8 ml (66.81 mmol) of allyl bromide in 5 ml of THF was then added dropwise. The reaction mixture was slowly warmed to RT overnight, and aqueous ammonium chloride solution was then added carefully. The mixture was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. This gave 10.7 g (83.5% of theory) of the target compound.GC-MS (Method 1): Rt=2.5 min; m/z=126 (M-C4H8)+.1H-NMR (400 MHz, DMSO-d6): delta=5.82 (m, 1H), 4.98 (d, 2H), 2.21 (d, 2H), 1.37 (s, 9H), 0.99 (q, 2H), 0.69 (q, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87661-20-9, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); A1;,
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Some common heterocyclic compound, 16519-02-1, name is Diethyl 2-fluoro-2-methylmalonate, molecular formula is C8H13FO4, 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 C8H13FO4

Diethyl 2-fluoro-2- methylmalonate (1 eq.) from the previous step was taken up in an aqueous pH=7.3 phosphate buffer (0.14 M, prepared by dissolving 7.3 g of NaHP04 and 2.1 g of KH2P04 per L of water). Lipase from Candida Rugosa (70 mg per mmol of substrate, 847 U/mg, Sigma Cat L1754) was then added and the resulting heterogeneous mixture was vigorously stirred at RT for 18 h. Depending on scale, occasional addition of 1 N NaOH was necessary to maintain the pH of the reaction mixture at -7.3 to ensure optimal activity. The reaction mixture was then added celite, stirred at RT for 1 h and filtered. The filtrate was extracted with EtOAc, dried over MgS04, and filtered. Concentration of the filtrate in vacuo furnished the desired product as a white, crystalline solid (71% yield, 93% enantiomeric excess).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 16519-02-1, its application will become more common.

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (125 pag.)WO2017/49069; (2017); A1;,
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Application of 29006-01-7, The chemical industry reduces the impact on the environment during synthesis 29006-01-7, name is Methyl 4-methoxybutanoate, I believe this compound will play a more active role in future production and life.

8-1. Preparation of Intermediate beta-Diketone Compound 1.8 mol of sodium hydride was added to the solvent ethylene glycol dimethyl ether, and 1 mol of methyl 4-methoxybutanoate was added thereto and stirred at room temperature for 10 minutes. Then, 1.2 mol of t-butylmethylketone was added to the solution which was then stirred at 92 C. for 19 hours. Then, the solution was cooled to room temperature and quenched in 36% hydrochloric acid, after which water and dimethylether were added to and mixed with the solution, and water was removed therefrom. The resulting organic material was washed with 1 wt % sodium hydroxide and then with saturated saline and concentrated, and the residue was fractionated, thereby obtaining the intermediate 8-methoxy-2,2-dimethyloctan-3,5-dione at a yield of 14%.

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

Reference:
Patent; CHO, Youn-Joung; WADA, Senji; CHOI, Jung-Sik; LEE, Jin-Seo; SAKURAI, Atsushi; CHO, Kyoo-Chul; YOSHINAKA, Atsuya; SATO, Haruyoshi; UEYAMA., Junji; YOSHINO, Tomoharu; SHIMIZU, Masako; US2012/251724; (2012); A1;,
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Electric Literature of 77820-58-7, 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. 77820-58-7, name is Methyl 2-amino-3-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 97 Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloroanthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for five hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15% sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67% yield, mp 56-68 C. IR and 1 H NMR spectra were in agreement with the assigned structure. Analysis: Calculated for C7 H8 ClNO: C, 53.35; H, 5.12; N, 8.88. Found: C, 53.16; H, 4.84; N, 9.28.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-3-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Dow Chemical Company; US4818273; (1989); A;,
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Reference of 25081-39-4,Some common heterocyclic compound, 25081-39-4, name is Methyl 3,5-dimethylbenzoate, molecular formula is C10H12O2, 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 2 Preparation of methyl-3,5-bis(bromomethyl)-benzoate A solution of methyl-3,5-dimethyl-benzoate (16.8 g, 0.10 mol) in carbon tetrachloride (150 ml) was treated with N-bromosuccinimide (35.6 g, 0.20 mmol), and benzoyl peroxide (500 mg, cat. amount), and heated to reflux. After 3 hours, the mixture was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was concentrated under reduced pressure and recrystallized from diethyl ether/hexanes (1:1) to yield the product (18.0 g, 55% yield) as a granular white solid. mp 64-70C. (lit. mp 65-69 C.); TLC (20% ethyl acetate/hexanes): Rf =0.65 (UV active, CAM stain)

The synthetic route of 25081-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Trustees of Columbia University in the City of New York; US5342934; (1994); A;,
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Ester – an overview | ScienceDirect Topics