Month: May 2021

Electric Literature of 167760-75-0, These common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)benzoate, 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.

6.54 g (30 mmol) methyl 4-amino-3-trifluoromethyl-benzoate are suspended in 50 ml 32% hydrochloric acid and cooled to -20 C. A solution of 2.28 g (33 mmol) sodium nitrite in 20 ml of water is added dropwise. The mixture is stirred for 3 hours at -20 to -10 C., then 27.08 g (120 mmol) tin-(II)-chloride dihydrate in 30 ml hydrochloric acid are added dropwise within 0.25 hours. The reaction mixture is stirred for 2 hours at -10 C., then acidified with cooling. The suspension is suction filtered through kieselguhr and washed with chloroform. The phases of the filtrate are separated, the aqueous phase is extracted with chloroform. The combined organic phases are dried and evaporated to dryness. The residue is precipitated as the hydrochloride, then stirred with diethyl ether. Yield: 4.02 g (50% of theoretical)

Statistics shows that Methyl 4-amino-3-(trifluoromethyl)benzoate is playing an increasingly important role. we look forward to future research findings about 167760-75-0.

Reference:
Patent; Breitfelder, Steffen; Maier, Udo; Hoenke, Christoph; Joergensen, Anne T.; Pautsch, Alexander; Brandl, Trixi; Grauert, Matthias; Hoffmann, Matthias; Scheuerer, Stefan; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/238730; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 61500-87-6, name is Methyl 2-amino-4-(trifluoromethyl)benzoate, 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. Safety of Methyl 2-amino-4-(trifluoromethyl)benzoate

Step 2: methyl 2-(acetylamino)-4-(trifluoromethyl)benzoate To a solution of the product from Step 1 (5.34 g) in dioxane (25 ml) was added acetic anhydride (6 ml) and pyridine (4 ml). After 60 hours of stirring at 80C, the solution was concentrated under reduced pressure and the residue was dissolved into ethyl acetate. The organic layer was washed with 2M sodium carbonate, 10% aqueous HCl, water and brine, dried over sodium sulfate and evaporated. The product was purified by flash chromatography (ISCO, 5%-20% ethyl acetate in hexanes) to provide a beige solid (5.27 g). LRMS (ES+) m/z 262.0 (M+H)+.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.R.L.; RUDD, Michael, T.; MCCAULEY, John; LIVERTON, Nigel; GRISE-BARD, Christiane; BROUCHU, Marie-Christine; CHARRON, Sylvie; AULAKH, Virender; BACHAND, Benoit; BEAULIEU, Patrick; ZAGHDANE, Helmi; HAN, Yongxin; FERRARA, Marco; HARPER, Steven; SUMMA, Vincenzo; CHACKALAMANNIL, Samuel; VENKATRAMAN, Srikanth; SHAH, Unmesh; VELAZQUEZ, Francisco; WO2013/74386; (2013); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 2967-93-3, 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. 2967-93-3 name is Methyl 2-fluoro-5-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.

(Table B1, B36, Scheme B2-B3) N-(3,4-dichlorobenzyl)-5-(((4,5-dihydro-1H-imidazol-2-yl)amino)methyl)-2-fluorobenzamide Bromination step: A solution of methyl 2-fluoro-5-methylbenzoate (2.10 g, 12.49 mmol) (CAS No.2967-93-3 Combi Blocks) in CCl4 (60 mL) was allowed to reflux through a Dean Stark trap to remove trace amounts of water. The solution was cooled to ambient temperature and treated with N-bromosuccinimide (NBS) (2.44 g, 13.74 mmol) and 2,2’azobis(2-methylpropionitrile (AIBN) (0.20 g, 1.20 mmol). The solution was heated to reflux for an 18 hour period. The mixture was cooled to ambient temperature, filtered and the resulting filtrate was concentrated under reduced pressure. The crude was then purified on silica gel using EtOAc/hexanes as mobile phase. The desired fractions where concentrated under reduced pressure to afford methyl 5-(bromomethyl)-2-fluorobenzoate compound 1.9 g (61%): 1H NMR (400 MHz, CDCl3) delta 8.0 (m, 1H), 7.6 (m, 1H), 7.1 (m, 1H), 4.5 (s, 2H), 4.0 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-fluoro-5-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Vanderbilt University; Gogliotti, Rocco D.; Stauffer, Shaun R.; Jeon, KyuOk; Salovich, James M.; Macdonald, Jonathan D.; Mills, Jonathan J.; Meyers, Kenneth M.; Alvarado, Joseph R.; Han, Changho; Fesik, Stephen W.; Lee, Taekyu; (177 pag.)US2020/55824; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 697762-67-7,Some common heterocyclic compound, 697762-67-7, name is Methyl 5-bromo-2-chloro-3-methoxybenzoate, molecular formula is C9H8BrClO3, 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 compound (74.80 g, 0.27 mol) obtained in Step 4 was dissolved in dichloromethane (300 ml) and 1M boran tribromide/dichloromethane solution (700 ml, 0.70 mol) was added dropwise at 10C or below. After completion of the addition, the mixture was stirred at room temperature for 1.5 hrs. The reaction mixture was added to ice water (1500 ml) and the precipitated solid was collected by filtration. The filtrate was partitioned, and the aqueous layer was extracted with ethyl acetate (200 ml). The organic layers were combined and concentrated under reduced pressure. The solid collected by filtration and the residue were dissolved in diethyl ether (1000 ml) and 1N aqueous sodium hydroxide solution (1000 ml) was added for extraction. 2N Hydrochloric acid (500 ml) was added to the aqueous layer. The mixture was stirred and extracted with ethyl acetate (800 ml). The mixture was partitioned and the organic layer was washed successively with water and saturated brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give an object product (63.83 g, yield 95%) as a beige solid.1H NMR(DMSO-d6 300MHz) (delta) ppm: 7.23 (1H, d, J=2.4Hz), 7.28 (1H, d, J=2.4Hz), 10.99(1H, s), 13.55 (1H, brs)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 5-bromo-2-chloro-3-methoxybenzoate, its application will become more common.

Reference:
Patent; Japan Tobacco Inc.; EP1564210; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H14O2

To a cooled solution (-40 C) of DIPEA (4.1 mL, 29.57 mmol, 2.1 eq) in THF (25 mL), was added w-BuLi (2.5M in hexanes, 1 1.2 mL, 28.36 mmol, 2 eq.) drop wise and the mixture was then stirred for 0.5 hr and then cooled to -78 C. Next, a solution of tert-butyl cyclopropanecarboxylate (2 g, 14.08 mmol, 1 eq.) in THF (5 mL) was added and the reaction mixture was stirred for 4 h at -78 C. 1-Propene, 3-bromo- (3.6 mL 42.25 mmol, 3 eq.) was added and reaction mixture was stirred for 2 h at -78 C. The reaction was then quenched with NH4Cl (30 mL) and extracted with DCM. The organic layer was dried over Na2S04 and concentrated to give tert-butyl 1-allylcyclopropane-l -carboxylate (1.5 g, 58 %). 1H NMR: (400 MHz, CDCl3) delta: 5.92-5.81 (m, 1H), 5.07-5.00 (m, 2H), 2.28 (d, J = 6.8 Hz, 2H), 1.45 (s, 9H), 1.15 (dd, J = 4.0, 3.2 Hz, 2H), 0.67 (dd, 4.0, 2.8 Hz, 2H).

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 87661-20-9.

Reference:
Patent; CAVION, INC.; RICHARDSON, Thomas E.; HIGGIN, Michelle; MACDONALD, Timothy; (102 pag.)WO2018/152317; (2018); 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. 2396-83-0, name is Ethyl hex-3-enoate, A new synthetic method of this compound is introduced below., Safety of Ethyl hex-3-enoate

A solution of 2.32 mL (14.5 mmol) ethyl (E)-hex-3-enoate in 30 mL dry dichloromethane under nitrogen was cooled to -78 C and 23.0 mL (23.0 mmol) DIBAL (1 m in dichloromethane) was added over 45 min. After stirring for 1 h methanol (8 mL) was added carefully, followed 50 mL of an aqueous citric acid solution (10 %, m/V). After warming up to room temperature 20 mL brine was added and the organic layer separated. The aqueous layer was extracted with dichloromethane (3 x 30 mL) and the combined organic layers dried over sodium sulfate and evaporated carefully (600 mbar, bath temperature 40 C). The liquid residue was treated with 1.14 g (16.4 mmol) hydroxylamine hydrochloride and 6.0 mL (6.0 mmol) sodium hydroxide solution (6 m) under ice cooling. The mixture was stirred for 4 h at room temperature, then 2 mL glacial acetic acid and 100 mL water added, followed by extraction with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate and evaporated. The residue was purified by FSC (dichloromethane) to give 0.865 g (7.64 mmol, 53%) of the oxime 3 as a 1:1 E/Z mixture as an unstable pale yellow oil.

The synthetic route of 2396-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lohrer, Bernhard; Bracher, Franz; Tetrahedron Letters; vol. 60; 51; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 57625-74-8, name is Methyl 2-methyl-2-phenylpropanoate, 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. Recommanded Product: Methyl 2-methyl-2-phenylpropanoate

(b) Reaction of Methyl-alpha,alpha-dimethylphenyl acetic acid with 4-Chlorobutyryl chlorideMethyl-alpha,alpha-dimethylphenylacetic acid on Fridel-Craft’s acylation with 4-chlorobutyryl chloride in presence of anhydrous aluminum chloride in ethylene dichloride produced acylated Methyl-alpha,alpha-dimethylphenyl acetic acid, i.e., ketone intermediate as meta and para- isomers.More particularly, aluminum chloride was taken in dichloroethane and cooled in between about 0 to 2O0C. To the above pre cooled solution, Methyl-alpha,alpha-dimethylphenyl acetic acid was added at low temperature. To the reaction mixture, 4-chlorobutyryl chloride was added between about 0 to 20C. After addition of acid chloride the reaction mixture was stirred for about 8 to 10 hours at the same temperature. After completion of the reaction, mixture was quenched over chilled mixture of potable water and cone, hydrochloric acid followed by stirring the reaction mixture for another 4 hours. The reaction mixture was washed with aqueous solution of sodium bicarbonate and finally with water. Removal of dichloromethane provided Methyl-4-(4-chloro-l-oxobutyryl)-alpha,alpha-dimethylphenyl acetate (Ketone) in about 95 % HPLC purity.EXAMPLE 2Methyl-4-(4-chloro-l-oxobutyryl)- a, a-dimethyl phenyl acetate (Ketone)95 Kg (0.7124 Kmole) of aluminium chloride was taken in 120 Ltr dichloroethane and reaction mixture was cooled to 0 to 2O0C. To it was added ester of example 1, 46 Kg (0.2584 Kmole) through addition flask, maintaining the temperature 0 to 200C. Finally, to the reaction mixture was added 80 Kg (0.5673 Kmoles) of 4-chlorobutyryl chloride through addition flask maintaining the temperature 0 to 200C. After addition of acid chloride stirred the reaction mixture at 0 to 200C for 8 to 10 hours. After completion it was quenched over chilled mixture of potable water and concentrated hydrochloric acid. Then stirred the reaction mixture at 0 to 200C for 4 hours and finally extracted in dichloroethane. It was washed with 10% w/v aqueous solution of sodium bicarbonate and finally with water. Removal of the solvent under vacuum provides thick oily mass of Methyl-4-(4-chloro-l-oxobutyryl)-alpha-alpha-dimethyl phenyl acetate (Ketone). HPLC purity = 95%. Yield = 65 to 70 Kg.

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

Reference:
Patent; WOCKHARDT LIMITED; JAWEED MUKARRAM, Siddiqui, Mohammed; MERWADE, Aravind, Yekanathsa; KHAN, Anjum, Reyaz; SOLANKI, Pawan, Vrajlal; WO2007/7347; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1731-79-9, A common heterocyclic compound, 1731-79-9, name is Dimethyl dodecanedioate, molecular formula is C14H26O4, 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.

EXAMPLE 4 [00088] The following Example describes the transesterification of dimethyl dodecanedioate using p-toluenesulfonic acid catalyst and the preparation of DDDA diester using a mixture of 50 mole % Exxal 13 and 50 mole % 1H, 1H, 5H-octafluoro-1-pentanol. [00089] A mixture of 51.68 g dimethyl dodecanedioate (0.2 mole), 41.58 g Exxal 13 (0.21 mole), 48.73 g 1H, 1H, 5H-octafluoro-1-pentanol (0.21 mole), and 0.38 g p-toluenesulfonic acid was heated, and methanol distilled off. When the reaction temperature reached 198 C., GC analysis showed the dimethyl dodecanedioate to be essentially gone, indicating that the reaction had gone nearly to completion. After cooling, the product was washed with brine, 1% aqueous NaOH, and water, then treated with basic alumina and filtered. The final acid number was 0.1 mg KOH/g. [00090] The same basic procedure was used to prepare other diesters, listed in Table 6. The non-fluorinated alcohol was Exxal 13 in all cases.[TABLE-US-00007] TABLE 6 DDDA diesters prepared according to Example 4. Mole fractionAcid PartiallypartiallynumberWt % FWt % FPrepara-Fluorinatedfluorinated(mg(elemental(bytionalcoholalcoholKOH/g)analysis)NMR) 30Telomer0.025 1.121.24 alcohol-L311H, 1H, 5H-0.50.1 octafluoro-1- pentanol321H, 1H, 2H,0.50.1 2H-perfluoro- 1-octanol331H, 1H0.50.1 heptafluoro- 1-butanol341H, 1H-0.50.1 perfluoro-1- octanol35Telomer0.0252 alcohol36Telomer0.0250.521.451.63 alcohol

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; E. I. du Pont de Nemours and Company; US6734320; (2004); B2;,
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. 191478-99-6, name is Methyl 4-amino-2,6-difluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 191478-99-6

4-(Chlorosulfonyl)benzoic acid (25.0 g, 113 mmol) and methyl 4-amino-2,6-difluorobenzoate (19.0 g, 101 mmol) were dissolved in methylene chloride (500 ml), and pyridine (25.0 ml, 285 mmol) was added thereto, followed by stirring at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure. The obtained residue was diluted with water, and then the pH was adjusted to 1.0 by adding 6 N hydrochloric acid. The precipitated solid was filtered, and washed with water. The obtained solid was resuspended in water, and washed with a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate (100 ml×2). The pH of the obtained aqueous layer was adjusted to 6.0 by adding 6 N hydrochloric acid thereto, followed by extraction with ethyl acetate (100 ml×2). The extraction liquids were combined, washed with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was removed to obtain the title compound (15.0 g, 36%). [0213] 1H NMR (d-DMSO, 400 MHz): delta 11.50 (s, 1H), 8.14 (d, J=8.4 Hz, 2H), 8.01 (d, J=8.4 Hz, 2H), 6.67 (d, J=10.4 Hz, 2H), 3.87 (s, 3H); MS (ESI) m/z 372 (M+H)+

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; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); 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. 18830-44-9, name is Methyl 3,3,3-trifluoropropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H5F3O2

Put 67.1g of sodium hydroxide and 300g of deionized water into a 500ml reaction bottle, cool the ice water bath to 5 10 , drop 216.6g of methyl trifluoropropionate above, control the internal temperature below 30 , and continue stirring after the dripping 30min.Concentrated hydrochloric acid was added dropwise to the reaction bottle until the pH of the reaction solution was below 2, and stirring was continued for 30 min after completion of the drop.300 g of dichloromethane was added to the reaction flask for extraction twice, and the dichloromethane was concentrated and recovered to obtain crude trifluoropropionic acid.Set up a vacuum distillation device, vacuum distillate crude trifluoropropionic acid, collect 83 ~ 85 fraction (vacuum degree -0.097MPa), which is 3,3,3-trifluoropropionic acid, weight 199g, purity 99.2%, yield 88.0%, total reaction yield 66.2%.

The synthetic route of 18830-44-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan Youse Chenzhoufu Chemical Co., Ltd.; Wang Gang; Peng Zhimin; Li Zhipeng; Yin Demei; Zhang Zhenhua; (8 pag.)CN110903183; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics