Author: Jessica.F

Application of 14920-81-1, 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. 14920-81-1, name is Methyl 2,6-dimethylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of methyl 2,6-dimethylbenzoate (described in J. Am. Chem. Soc., 99, 6405 (1977); 23.4 g, 143 mmol) in dichloroethane (200 ml) were added N-bromosuccinimide (25.46 g, 143 mmol) and alpha,alpha’-azobisisobutyronitrile (234.8 mg, 1.43 mmol), and the mixture was irradiated with visible light (tungsten lamp, 375 W) for 1 hour. After cooling the reaction mixture, the precipitated material was filtered off, and the solvent was distilled off under reduced pressure. The obtained oily residue was subjected to chromatography on a silica gel (200 g) column (eluent; ethyl acetate : hexane = 1 : 10) to give an oily mixture containing ca. 50% methyl 2-(bromomethyl)-6-methylbenzoate. The mixture was dissolved in dimethyl sulfoxide (150 ml), and sodium acetate (16.4 g, 0.2 mol) was added thereto. The resulting mixture was stirred at room temperature for 2 hours, then a saturated aqueous solution of ammonium chloride was added thereto, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (200 g) column (eluent; ethyl acetate : hexane = 1 : 10 ~ 1 : 3) to give methyl 2-(acetoxymethyl)-6-methylbenzoate (8.09 g, more than 80% content) as a colorless oil. The obtained methyl 2-(acetoxymethyl)-6-methylbenzoate was used for the following reaction without further purification. NMR spectrum (400 MHz, CDCl3) delta ppm: 2.07 (3H, s), 2.38 (3H, s), 3.92 (3H, s), 5.15 (2H, s), 6.99-7.12 (3H, m). Methyl 2-(acetoxymethyl)-6-methylbenzoate obtained above was dissolved in methanol (80 ml), and potassium carbonate (251.5 mg, 1.8 mmol) was added thereto. The mixture was stirred at room temperature for 2 hours, then a 2N aqueous solution of hydrochloric acid (3 ml) was added thereto, and the solvent was distilled off under reduced pressure. The obtained solid residue was dissolved in ethyl acetate, and the solution was washed with a saturated aqueous solution of sodium chloride and then the solvent was distilled off under reduced pressure. The solid residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate : hexane = 1 : 2) to afford 7-methyl-1(3H)-isobenzofuranone (5.18 g, more than 80% content). The obtained 7-methyl-1(3H)-isobenzofuranone was used for the following reaction without further purification. NMR spectrum (400 MHz, CDCl3) delta ppm: 2.71 (3H, s), 5.23 (2H, s), 7.25-7.30 (2H, m), 7.56 (1H, t, J=8 Hz). A solution of the 7-methyl-1(3H)-isobenzofuranone obtained above in tetrahydrofuran (80 ml) was cooled to 0C, and lithium borohydride (1.90 g, 87.2 mmol) was added thereto. The mixture was stirred at 60C for 2 hours, then cooled to 0C, and a 2N aqueous solution of hydrochloric acid (50 ml) was added dropwise. The product was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (75 g) column (eluent; ethyl acetate : hexane = 2 : 1 ? 1 : 0) to afford the title compound (4.17 g, 19% total yield from methyl 2,6-dimethylbenzoate) as an oil. NMR spectrum (400 MHz, CDCl3) delta ppm: 2.45 (3H, s), 4.76 (2H, s), 4.79 (2H, s), 7.17-7.22 (3H, m) IR spectrum nu max CHCl3 cm-1: 3605, 1469, 1380, 1002 Mass spectrum m/z (EI): 152 (M+).

The synthetic route of Methyl 2,6-dimethylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sankyo Company, Limited; EP1362856; (2003); 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 61500-87-6 as follows. Safety of Methyl 2-amino-4-(trifluoromethyl)benzoate

General procedure: To a solution of methyl 2-amino-4-fluorobenzoate (1.64 g, 9.71 mmol) and methanesulfonyl chloride (5.28 mL, 115 mmol) in dichloromethane (100 mL) was added pyridine (7.86 mL, 97.1 mmol). The solution was stirred at room temperature for 18 hours. The reaction was quenched with 1N HCl and was stirred for 5 minutes. The mixture was extracted with DCM (3×). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography to afford methyl 4-fluoro-2-(methylsulfonamido)benzoate.

According to the analysis of related databases, 61500-87-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Sciences, Inc.; Farand, Julie; Kaplan, Joshua A.; Notte, Gregory; Olen, Casey Lockwood; Sangi, Michael; Sperandio, David; (115 pag.)US2019/359565; (2019); A1;,
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Synthetic Route of 79432-87-4, A common heterocyclic compound, 79432-87-4, name is (E)-Methyl 3-(3-bromophenyl)acrylate, molecular formula is C10H9BrO2, 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.

To a dry flask were added (E) -methyl 3- (3-bromophenyl) acrylate (1.18 g, 4.89 mmol) , methanol (10 mL) and 10%Pd/C (120 mg) in turn, the mixture was stirred at 40 under H2for 6 hours. The mixture was filtered and the filtrate was concentrated in a rotary evaporator to get the title compound as a brown liquid (1.2 g, 100%) . ESI: (ESI, pos. ion) m/z: 243.1 [M+H]+.

The synthetic route of 79432-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
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Related Products of 636-53-3, These common heterocyclic compound, 636-53-3, name is Diethyl isophthalate, 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.

Will 6.8Kg of diethyl isophthalate, 24.0 kg of 2,2,6,6-tetramethyl-4-aminopiperidine was added to a 50 liter reactorIn the reactor all the materials off the entrance. The reaction was carried out at 190 C for 2 hours and then at 230 C for 6 hours. The temperature was lowered to below 180 C, and excess 2,2,6,6-tetramethyl-4-aminopiperidine was recovered by vacuum distillation under a vacuum pump. Then use water to generateN, N’-bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,3-benzenedicarboxamide, filtered and dried to give 12.4 kg of acicular white crystalline product , Yield 91.6%.

Statistics shows that Diethyl isophthalate is playing an increasingly important role. we look forward to future research findings about 636-53-3.

Reference:
Patent; Xiangtan University; Luo Zhiqiang; Zhang Lingjun; Zhang Jing; Ji Yongsheng; Ji Changfu; Zeng Yang; Liu Mengyan; Zhou Ji; Liu Minna; Wang Zhe; (7 pag.)CN106905225; (2017); A;,
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Reference of 25081-39-4, 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. 25081-39-4, name is Methyl 3,5-dimethylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step CC: (R)-3-(3,5-dimethylbenzoyl)-4-methyldihydrofuran-2-one To a solution of (R)-4-methyldihydrofuran-2-one (1.68 g in 40 mL dioxane) were added 5.51 g 3,5-dimethylbenzoic acid methyl ester followed by 1.82 g sodium hydroxide and the mixture heated to reflux on an oil bath. After 3 hours, the mixture was cooled to room temperature and the pH neutralized by the addition of 0.5N hydrochloric acid. The mixture was then extracted with ethyl acetate and the organic portion washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 9:1) gave the title compound (2.42 g).

The synthetic route of Methyl 3,5-dimethylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6017944; (2000); A;; ; Patent; Merck & Co., Inc.; US6159975; (2000); A;; ; Patent; Merck & Co., Inc.; US5985901; (1999); A;,
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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. 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, A new synthetic method of this compound is introduced below., Formula: C12H12O6

EXAMPLE 5 STR20 1,3,5-tris(hydroxymethyl)benzene To a stirring solution of trimethyl 1,3,5-benzenetricarboxylate (10.45 g, 41.4 mmol) in 70 ml of anhydrous THF is added at room temperature a 10M solution of borane-methyl sulfide complex (25 ml, 248 mmol) and the solution is heated to reflux for 3 h. The mixture is then added slowly to 50 ml of MeOH and the resulting mixture is heated at 70 C. for 10 min to remove the methyl sulfide. Evaporation of solvent, washing twice with 50 ml of MeOH and evaporation of MeOH gives 1,3,5-tris(hydroxymethyl)benzene (6.96 g, 100%). 1 H NMR (D2 O): delta 4.52 (6H, s), 7.15 (3H, s).

The synthetic route of 2672-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Frosst Canada & Co.; US6121253; (2000); A;,
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Electric Literature of 6942-39-8,Some common heterocyclic compound, 6942-39-8, name is Methyl 2-bromo-5-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

a) 2-Bromo-5-dimethylamino-benzoic acid methyl ester (16a) To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-5-fluoro-benzoic acid methyl ester (Rarechemicals) and 60.0 ml dimethylsulphoxid are added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture is stirred for 11h at 70C in an autoclave and is concentrated with high vacuum rotation evaporator at 65C. The residue is diluted with dichloromethane, washed twice with water. The combined water phases are extracted with dichloromethane. The combined dichloromethane phases are washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude is purified by column chromatography and the desired product 16a is obtained in 70 % yield (4,08 g, 15.8 mmol). MS-ESI: 258/560 (M+ +1, 90/81).

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

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1897885; (2008); 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. 111-79-5, name is Methyl non-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 111-79-5

[0080] Example 7 – Hydrogenation of esters using complexes 1[0081] tBuOK (15 mg, 0.13 mmol) was added to a solution of complex 1 (51 mg, 0.10 mmol) in 10 mL of THF and the mixture was stirred for 3 min. 1 mL of the obtained solution was mixed with methyl benzoate (2.72 g, 20.0 mol) or other desired substrate in 6 mL of THF or toluene. The mixture was then placed into a 75 mL stainless-steel reactor (Parr 4740) equipped with a magnetic stir bar. The reactor was purged by two cycles of pressurizati on/venting with H2 (150 psi, 10 Bar) and then pressurized with H2 (725 psi, 50 Bar) and disconnected from the H2 source. The reaction was conducted for 1.5 h at 100 C in a preheated oil bath. At the end of the reaction time, the reactor was placed into a cold water bath and it was depressurized after cooling to the ambient temperature. The product benzyl alcohol was obtained after evaporation of all volatiles (THF, CH3OH) under vacuum. The results are shown in tables 1-4 below. See table 2 for a complete list of tested substrates.

The synthetic route of 111-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GOUSSEV, Dmitri; SPASYUK, Denis; WO2013/23307; (2013); 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. 3681-71-8, name is cis-3-Hexenyl acetate, A new synthetic method of this compound is introduced below., Safety of cis-3-Hexenyl acetate

A mixture of (Z)-hex-3 -en- 1 -yl acetate(4) 9m (0.124 g, 0.87 mmol), aminating agent la (0.208 g, 1.04 mmol), and Rh2(esp)2 (6.6 mg, 1 mol%) was stirred at rt in CF3CH2OH (8 mL). Three additional portions of catalyst (6.6 mg, 1 mol %) were added every 12 h thereafter for a total of 26.4 mg (35 //mol, 4 mol%). After a total of 51 h, the reaction mixture was quenched and chromatographically purified on a CombiFlash system using 80-100% EtOAc/hexanes as eluent to afford the title tetrahydrofuran as a viscous oil (84 mg, 61%) obtained as a mixture of diastereomers (>95:5). TLC: Rf~ 0.3 (80% EtOAc/hexanes); XH NMR (400 MHz, CDC13) (major diastereomer) delta 4.23 (ddd, J= 8.7, 6.7, 4.3 Hz, 1H), 3.77-3.67 (m, 2H), 3.58-3.50 (m, 1H), 3.19 (br s, 1H), 1.92 (s, 3H), 1.87-1.68 (m, 2H), 1.63-1.37 (m, 2H), 0.90 (t, J= 7.5 Hz, 3H); 13C NMR (101 MHz, CDC13) delta 163.98, 82.16, 72.85, 58.89, 38.28, 28.28, 14.04, 9.84; HRMS (ESI+) Calcd. for [C8Hi5N02+H]+ 158.1 176, Found 158.1173; IR (neat) 3272, 2963, 2935, 1668 cm”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; ESS, Daniel, Halsell; FALCK, John, Russell; JAT, Jawahar, Lal; URTI, Laszlo; WO2015/103505; (2015); A2;,
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Electric Literature of 24393-53-1,Some common heterocyclic compound, 24393-53-1, name is (E)-Ethyl 3-(4-bromophenyl)acrylate, molecular formula is C11H11BrO2, 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.

To a solution of (£ ethyl 3-(4-bromophenyl)acrylate (10.0 g, 39.2 mmol) in THF (150 mL) was slowly added at -78 C a solution of DIBA1-H (86 mL of 1M solution in hexanes, 86.0 mmol). The resulting solution was then allowed to slowly warm to 0 C, after which a further 10 mL of DIBA1-H solution was added. TLC analysis indicated complete reaction and the mixture was re-cooled to -78 C. MeOH was then slowly added to quench the remaining reducing agent and the mixture allowed to warm back to rt over 30 minutes. The resulting mixture was poured into a saturated aqueous solution of Rochelle’s salt and then extracted with EtOAc. The organic phase was separated, dried (MgSO i), filtered and the filtrateconcentrated in vacuo. The crude product thus obtained was purified on silica eluting with a gradient of 0 to 35% EtOAc in hexanes to afford 6.0 g (71%) of (£)-3-(4-bromophenyl)prop-2-en-l-ol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (E)-Ethyl 3-(4-bromophenyl)acrylate, its application will become more common.

Reference:
Patent; INCEPTION 2, INC.; STOCK, Nicholas, Simon; CHEN, Austin, Chih-Yu; BRAVO, Yalda, Mostofi; JACINTHO, Jason, Duarte; SCOTT, Jill, Melissa; STEARNS, Brian, Andrew; CLARK, Ryan, Christopher; TRUONG, Yen, Pham; WO2013/134562; (2013); A1;,
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