Tag: M.W=200-300

Synthetic Route of 41841-16-1, 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. 41841-16-1 name is Methyl 2-(4-bromophenyl)acetate, 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.

Preparation of Intermediate methyl 1-(4-bromoDhenyl)cvclobutanecarboxylate (1AH-1); Sodium hydride (3.5g, 88mmol) was stirred as a suspension in dimethylformamide (250ml) under argon. This was warmed to 35C and methyl 2-(4-bromophenyl)acetate (10g, 44mmol) in dimethylformamide (10OmL) was added drop wise over 1 hour and then stirred at 300C for 1 hour. To this the 1 ,3-dibromopropane (4.4ml, 44mmol) in dimtheylformamide (50ml) was added drop wise over 1 hour, and this was left to stir at room temperature overnight. The reaction was incomplete. Sodium hydride (3.5g, 88mmol) was prepared in dimethylformamide (100ml) at 35C and was added to this drop wise to the reaction mixture over 1 hour. This was again left to stir at room temperature overnight. Saturated aqueous ammonium chloride solution (200ml) was carefully added, followed by water (500ml). The product was extracted with ethyl acetate (2 x 500ml), washed with water (3 x 500ml), and brine (2 x 500ml). The organic solution was then dried over magnesium sulfate, filtered, and evaporated. The crude product was purified by flash chromatography (12.5% ethyl acetate in heptane)to methyl 1-(4-bromophenyl)cyclobutanecarboxylate (900mg, 3.3mmol, 7.5%).1 H NMR (400MHz CDCI3) 7.45 (d, 2H), 7.15 (d, 2H), 3.65 (s, 3H), 2.80 (m, 2H), 2.45 (m, 2H), 2.05 (m 1 H), 1.85 (m, 1 H)

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

Reference:
Patent; PFIZER INC.; ASPNES, Gary, Erik; DOW, Robert, Lee; MUNCHHOF, Michael, John; WO2010/86820; (2010); A1;,
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Reference of 46064-79-3, A common heterocyclic compound, 46064-79-3, name is Methyl 3-amino-4-bromobenzoate, molecular formula is C8H8BrNO2, 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.

The intermediate compound prepared in step 4 (100 mg, 0.26 mmol) to N, N-dimethylformamide (2.6 ml) was addedAnd methyl 3-amino-4-bromobenzoate (59.8 mg, 0.26 mmol)And bis (triphenylphosphine) palladium (II) dichloride (21 mg, 0.03 mmol),Copper (I) iodide (5.7 mg, 0.03 mmol),Triethylamine (0.1 ml, 0.8 mmol) was added thereto, followed by stirring at 80 C for 4 hours.The reaction mixture was diluted with ethyl acetate and washed with distilled water.Dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to obtain the intermediate compound methyl 3-Amino-4 – ((2-chloro-4 – ((5- cyclopropyl-3- (2,6-dichlorophenyl)Isoxazol-4-yl) methoxy)Phenyl) ethynyl) benzoate (98.9 mg, 67%).

The synthetic route of 46064-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ildong Pharmaceutical Co., Ltd.; Kang Jae-hun; Lee Hong-seop; Lee Yun-seok; Jeong Jin-a; Kwon Seong-uk; Kim Gyeong-seon; Song Dong-geun; Choi Ji-hye; Hwang Hye-min; (43 pag.)KR2018/115126; (2018); A;,
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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. 116419-94-4, name is Methyl 4-methyl-3-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

To a solution of methyl-4-methyl-3-(trifluoromethyl) benzoate (1 equiv) in chloroform was added N-bromosuccinimide (1.1 equiv) and benzoyl peroxide (0.01 equiv). The reaction mixture was heated at reflux overnight (18h). It was then cooled to room temperature, washed with water, dried over Na2S0 and concentrated. It was purified by silica gel chromatography (eluted with 1% ethyl acetate/hexane) to provide the title compound (65% yield). ESI MS m/z -297.

According to the analysis of related databases, 116419-94-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; KOMPELLA, Amala; GAMPA, Venugopala Krishna; GANGANAMONI, Srinivasulu; SIRIGIREDDY, Balakrishna Reddy; ADIBHATLA, Kali Satya Bhujanga Rao; NANNAPANENI, Venkaiah Chowdary; WO2015/186137; (2015); 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. 91085-56-2, name is Ethyl 3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 3,5-dichlorobenzoate

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 ml of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3,5-Dichloro-benzoic acid ethyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(3,5-Dichloro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.5 g, 4.8 mmol) as brown solid in 34% yield.

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; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); A1;,
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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. 20330-90-9, name is Dimethyl 5-chloroisophthalate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Dimethyl 5-chloroisophthalate

To a solution of 1,3-dimethyl 5-chlorobenzene-l ,3-dicarboxylate (4.00 g, 17.5 mmol) in dioxane (50 mL) and water (50 mL) was added NaOH (700 mg, 17.5 mmol). The resulting suspension was stirred vigorously at 40C for 2 hrs and then for a further 16 hrs at room temperature. The reaction mixture was evaporated to dryness, re-dissolved in water (-200 mL) and acidified to pH 3 using 1M HCl. The resulting white precipitate was sonicated for 2 mins and filtered. The white solid was washed further with water and then dried in a vacuum oven overnight. This afforded a white solid (3.6 g) which was a mixture of 3 products including 3-chloro-5-(methoxycarbonyl)benzoic acid. This solid was dissolved in DMF (150 mL) at 0C and diethylamine (2.56 g, 0.03 mol), DIPEA (6.09 ml, 0.03 mol) and HATU (6.64 g, 0.02 mol) were added. The reaction mixture was then stirred at room temperature for 6 hrs then evaporated to dryness, re- dissolved in EtOAc (200 mL) and washed with water (3 x 200 mL) and brine (2 X200 mL). The combined organics were then dried over MgSC>4 and evaporated to dryness to afford the crude product. This was purified by silica chromatography (Biotage: lOOg SNAP cartridge) eluting with 0-80% EtOAc in heptane to afford the title compound as a colourless oil (880 mg (28%); H NMR (500 MHz, CDC13) 5 1.13 (br. s, 3H), 1.26 (t, 3H), 3.24 (br.s, 2H), 3.54 (br. s, 2H), 3.93 (s, 3H),7.55 (m, 1H), 7.92 (m, 1H), 8.04 (m, 1H).

The synthetic route of 20330-90-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTIVE BIOTECH AB; FRITZSON, Ingela; LIBERG, David; EAST, Stephen; MACKINNON, Colin; PREVOST, Natacha; WO2014/184234; (2014); A1;,
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Related Products of 17100-65-1, A common heterocyclic compound, 17100-65-1, name is Methyl 2-bromo-4-methoxybenzoate, molecular formula is C9H9BrO3, 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.

Methyl 2-bromo-4-methoxybenzoate(45 mg, 1.4 equiv), BINAP (50 mg, 0.08 equiv), Pd (OAc) 2 (11.2 mg, 0.05 equiv) ), Toluene 20mL, N2 protection, 110 , the reaction 18h, filtered and the solvent was recovered, column chromatography to give a solid 165mg, yield 57%.

The synthetic route of 17100-65-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Shanghai Jiao Tong University; He Qiuqin; Yin Ming; Fan Renhua; Han Dandan; Zhou Kaiyi; Song Runzhe; Zhao Lu; (11 pag.)CN107056702; (2017); A;,
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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 120-51-4 as follows. Computed Properties of C14H12O2

General procedure: A mixture of amine (6.0 mmol), ester (3.0 mmol) and Ru-MACHO (1% mol) in toluene (3.0 mL) was placed in a flask and replaced withnitrogen gas. Then, t-BuOK (20% mol) was added in the mixture in the nitrogen gas flowing. The mixture was heated by reflux under the nitrogen atmosphere. During this time, the nitrogen gas was passed through the Schlenk line allowing the hydrogen gas to evolve from the reaction to escape the reactor. After the 48 h, the solvent was evaporated and the crude product was purified by flash chromatography on silica-gel to give the desired amides in 55-98% yields. The structures of the obtained amide swere determined by FT-IR and 1HNMR.

According to the analysis of related databases, 120-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Han, Qian; Xiong, Xingquan; Li, Sizhong; Catalysis Communications; vol. 58; (2014); p. 85 – 88;,
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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. 34529-06-1, name is Dimethyl 3-aminophthalate, A new synthetic method of this compound is introduced below., Product Details of 34529-06-1

3-Pentylamino-phthalic acid dimethyl ester To a stirred solution of 3-amino-phthalic acid dimethyl ester (3.14 g, 15 mmol) in methylene chloride (50 ml) under a nitrogen atmosphere were added valeraldehyde (2.0 ml, 18.75 mmol) and acetic acid (5.18 ml, 90 mmol). The mixture was stirred for 5 minutes followed by addition of sodium triacetoxyborohydride (6.36 g, 30 mmol). The reaction was stirred for 30 minutes, diluted with methylene chloride (50 ml), washed with water (2*100 ml), saturated aqueous sodium bicarbonate (2*100 ml), brine (100 ml), and dried (MgSO4). The solvent was evaporated in vacuo to give 4.19 g of product (100%) that used without further purification. 1H NMR (DMSO-d6) d 7.31 (t, J=7.9 Hz, 1H), 6.81-6.75 (m, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 3.15 (bs, 2H), 1.68-1.60 (m, 2H), 1.45-1.32 (m, 4H), 0.89 (t, J=6.9 Hz, 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; Robarge, Michael J.; Chen, Roger Shen-Chu; Muller, George W.; Man, Hon-Wah; US2003/96841; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 82702-31-6, name is Methyl 3-bromo-4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6BrFO2

Step 1: To methyl 3-bromo-4-fluorobenzoate (3.02 g, 13.0 mmol) in ether (30 ml) at 0 C. add dropwise MeMgBr (3.0M in ether, 11 ml, 33 mmol). Stir 1 h and pour onto ice. Acidify with 1N HCl, separate the ether, wash with 1N NaHCO3, dry (MgSO4), and concentrate to obtain the product as a colorless oil

The synthetic route of 82702-31-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Corporation; US2004/220194; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 26759-46-6

Example 1: (Production of 6,7-dimethoxyquinazolin-4-one); Using acetic acid and an inorganic base, ammonia, as a catalyst, 6,7-dimethoxyquinazolin-4-one was produced in the manner mentioned below. 0.84 g (4 mmol) of methyl 4,5-dimethoxyanthranilate, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.05 g (2.8 mmol) of ammonia from a pressure cylinder were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with methanol and then dried in vacuum at 70C for 2 hours to obtain 0.77 g of a crystal. The obtained crystal was analyzed for the purity by high-performance liquid chromatography, and its purity was 99.5 %; and 6,7-dimethoxyquinazolin-4-one was obtained at a yield of 93.0 %. The result is shown in Table 1. Examples 2 to 4, and Comparative Examples 1 and 2: (Production of 6,7-dimethoxyquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 1, for which, however, the catalyst was changed as in Table 2. In Example 4, ammonium acetate was used as the catalyst; and in Comparative Examples 1 and 2, formic acid or potassium carbonate, respectively, was used alone as the catalyst like in JP-A 2002-338550 (Patent Reference 4). From the results in Table 1, it is known that the reaction system with acetic acid and a base coexisting therein of the present invention gives 6,7-dimethoxyquinazolin-4-one at a higher yield than the conventional reaction system with formic acid or potassium carbonate alone therein.

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP1997812; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics