Category: esters-buliding-blocks

Application of 55666-42-7, The chemical industry reduces the impact on the environment during synthesis 55666-42-7, name is tert-Butyl 2-bromobenzoate, I believe this compound will play a more active role in future production and life.

Step 2 tert-butyl 4′-fluoro-3′-methyl-[1,1′-biphenyl]-2-carboxylate Tert-butyl 2-bromobenzoate (33.38 g, 129.8 mmol), (4-fluoro-3-methylphenyl)boronic acid (10 g, 64.9 mmol), Pd(PPh3)4(749 mg, 0.64 mmol), and Na2CO3 (13.7 g, 129.8 mmol) were dissolved in IPA (50 ml) and H2O (50 ml) in a 1 L flask, followed by reflux-stirring for 12 hours. The reaction mixture was concentrated under reduced pressure. The organic layer was separated by using ethyl acetate and brine. The separated organic layer was dried over MgSO4 and filtered. The mixture was separated by column chromatography to give tert-butyl 4′-fluoro-3′-methyl-[1,1′-biphenyl]-2-carboxylate (13 g).

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, tert-Butyl 2-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hyundai Pharm Co., Ltd.; LEE, In Hee; CHAE, Hee Il; KIM, Se hoan; MOON, Soon Young; HA, Tae Young; CHOI, Hyo sun; KIM, Young Seok; KIM, Chun hwa; RHEE, Jae Keol; (132 pag.)US2016/355483; (2016); A1;,
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Application of 5048-82-8, 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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows.

Step 7; Ethyl (2E)-3 (4-{ [(1-aminocyclopentyl)carbonyl]amino}phenyl)acrylate; 1-{[benzyloxy)carbonyl]amino}cyclopen(anecarboxylic acid was dissolved in DMF (0.2 M). HATU (1 eq.) and triethylamine (3 eq.) were added, followed by ethyl cinnamate (0.95 eq.). The resulting mixture was stirred for 48 h at 40 °C. DMF was evaporated, the resulting oil taken up in EtOAc and the solution washed with HQ (3x, 1 M), water, a solution of saturated aqueous NaHC03 (2x) and brine. Drying over Na2SO4 and evaporation gave an orange solid, which was purified by flash chromatography on silica gel using PE/EtOAc (2.5 : 1. containing 1percent EtOH) as the eluent The resulting solid was immediately dissolved in DCM (0,1 M) and triflic acid (5 eq.) was added dropwise at RT, After 5 mm at RT, the red mixture was poured into an aqueous solution of NaHCOj. The organic phase was separated, the aqueous phase was extracted with DCM (4x) and the combined organic phases dried over Na2SO4. Evaporation gave the title compound as an off-white solid, which was used without further purification.

The chemical industry reduces the impact on the environment during synthesis Ethyl 3-(4-aminophenyl)acrylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA; WO2006/29912; (2006); A1;,
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Synthetic Route of 110104-60-4,Some common heterocyclic compound, 110104-60-4, name is (E)-Methyl 4-chloro-3-methoxybut-2-enoate, molecular formula is C6H9ClO3, 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 mixture of 4-phenoxyaniline (10 g) and acetonitrile (40 mL) was added a mixture of methyl 4-chloro-3-methoxy-2-(E)-butenoate (9.18 mL) and acetonitrile (40 mL) at 0 C. To the reaction mixture was added a mixture of triethylamine (8.28 mL) and acetonitrile (20 mL) at 0 C. The reaction mixture was heated under reflux for 4 hr and cooled to room temperature. The precipitate was removed by filtration. To the filtrate was added water (80 mL), and the mixture was adjusted to pH 3 with concentrated hydrochloric acid. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. To the residue were added toluene (80 mL) and acetic acid (2.0 mL) at room temperature. The reaction mixture was heated at 50 C. for 1.5 hr. The reaction mixture was diluted at room temperature with water, saturated brine and saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (7.43 g). MS: [M+H]+ 281.8.

The synthetic route of 110104-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KOIKE, Tatsuki; FUSHIMI, Makoto; AIDA, Jumpei; IKEDA, Shuhei; KUSUMOTO, Tomokazu; SUGIYAMA, Hideyuki; TOKUHARA, Hidekazu; (170 pag.)US2016/318864; (2016); A1;,
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Synthetic Route of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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 2,4-difluorobenzoic acid (950 mg, 6 mmol) was dissolved in 2 ml of thionyl chloride,Heated to 80 C reflux2 hours,After completion of the reaction, the solvent was dried to give an oily compound,The oily compound was placed on an oil pump for half an hour,Immediately put the next step.The compound of the previous step was quickly dissolved in dry toluene,And ethyl 3- (dimethylamino) acrylate (1 g, 7 mmol) was added,Triethylamine (1.01 g, 10 mmol)Heated to 90 C,Fully stirred for 12h,Cooled to room temperature, spin dry solvent, dissolved in ethyl acetate and washed several times with water,After concentration, the compound 1a (1.42 g, 85%) was obtained as a yellow oil by column chromatography elution (petroleum ether: ethyl acetate = 10: 1 to 2: 1).

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Geng Meiyu; Li Bowen; Ai Jing; Xu Zhongliang; (65 pag.)CN107151240; (2017); 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. 2557-13-3, name is Methyl 3-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Methyl 3-(trifluoromethyl)benzoate

3-trifluoromethyl-benzoic acid methyl ester fluoride to 4.30g (21.1mmol)Cesium 92.6mg the (0.696mmol) added under an argon atmosphere, then cooled to -10 or less of. This trifluoromethyl trimethylsilane about 4mL (about 27mmol) was added dropwise at -10 or less. 1 hour at -10 C., further stirred for 1 hour at room temperature. Then extracted by the addition of methylene chloride and water to the reaction solution. The organic phase is dried over magnesium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (developing solvent = n-hexane / ethyl acetate = 98/2 [volume]). Concentration collect a portion corresponding to Rf value of about 0.9, as a colorless transparent liquid trimethyl (2,2,2-trifluoro-1-methoxy-1- (3- (trifluoromethyl) phenyl) ethoxy) silane 4.46g (65%) obtained. Incidentally, Rf is selected from the group consisting of the ratio of distance traveled from the origin with respect to the distance from the origin to the solvent front of the sample of interest (relative moving distance).

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; NIPPON SODA COMAPNY LIMITED; ITO, YOSHIKAZ; KUBOTA, YASUSHI; ICHINARI, DAISUKE; INOUE, HIROKI; IWATA, JYUN; NAKASHIMA, RYOYO; KURUSHIMA, HIROAKI; MATSUDA, KEIICHIRO; KUTOSE, KOICHI; (90 pag.)JP5653442; (2015); B2;,
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Electric Literature of 89-91-8,Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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.

j00399j A mixture of(3,4-difluorophenyl) methanamine (2.0 g, 14 mmol) and methyl 2,2- dimethoxyacetate (3.8 g, 28 mmol) was stirred at 140 C for 1 hour in the microwave. On completion, the reaction mixture was diluted with dichloromethane (20 mL) and concentrated in vacuo to give cmde compound B-64 (4.3 g, crude) as a yellow solid. LCMS (E): tR=0.596 mi, (ES) mlz (M+H) =246.1.

The synthetic route of 89-91-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
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Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, 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. Product Details of 106896-49-5

A flame-dried flask, equipped with a reflux condensor, containing methyl 4- amino-3-bromobenzoate (2.5 g, 10.87 mmol), bis(neopentyl glycolato)diboron (3.07 g, 13.58 mmol), potassium acetate (3.20 g, 32.6 mmol), and PdC^dppf -CH^C^ adduct(0.222 g, 0.272 mmol) was added degassed DMSO (31.0 mL). The resulting dark red- brown suspension was warmed to 85 C. After 2.5 h, the resulting dark black reaction was cooled to RT and poured into cold water (100 mL) to give a suspension. The suspension was extracted with EtOAc (3x). The combined organic layers were washed with sat. aHC03, brine, dried over sodium sulfate, filtered and concentrated to give a brown solid weighing 3.1 g. Purification by normal phase chromatography gave 1.64 g (55%) of Intermediate 39 as a pale, yellow solid. lH NMR (500 MHz, CDC13) delta ppm8.35 (d, J=2.20 Hz, 1 H), 7.84 (dd, J=8.53, 2.20 Hz, 1 H), 6.52 (d, J=8.53 Hz, 1 H), 5.25 (br. s., 2 H), 3.84 (s, 3 H), 3.79 (s, 4 H), 1.03 (s, 6 H). MS (ESI) m/z: 196.0 (M-C5H8+H)+

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James, R.; FANG, Tianan; DECICCO, Carl, P.; PINTO, Donald, J., P.; ROSSI, Karen, A.; HU, Zilun; JEON, Yoon; QUAN, Mimi, L.; SMALLHEER, Joanne, M.; WANG, Yufeng; YANG, Wu; WO2011/100401; (2011); A1;,
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Electric Literature of 61500-87-6, 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. 61500-87-6, name is Methyl 2-amino-4-(trifluoromethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows.

2-Amino-4-trifluoromethyl-benzoic acid methyl ester, (48 g, 219 mmol) was dissolved in MeOH (750 ml). Silver sulfate (68.3 g, 219 mmol) and iodine (55.6 g, 219 mmol) was added and rinsed in with MeOH (50 ml). The reaction mixture was left for 1 hour at RT. The reaction mixture was filtered under vacuum and the filtrate concentrated in vacuo. The residue was taken up in MeOH (100 ml) and water (10 ml) and the mixture heated at 80C. The crude solution was hot filtered to remove residual inorganics and the warm filtrate was poured slowly into water (750 ml) with vigorous stirring. The mixture was left to particulate for 10 minutes and filtered to give the title compound as an orange solid. MS m/z 345[M+H]+.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-4-(trifluoromethyl)benzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BALA, Kamlesh, Jagdis; BUDD, Emma; EDWARDS, Lee; HOWSHAM, Catherine; LEGRAND, Darren, Mark; TAYLOR, Roger, John; WO2013/38390; (2013); A1;,
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These common heterocyclic compound, 55954-25-1, name is Methyl 2-(2,4-Dimethoxyphenyl)acetate, 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. Product Details of 55954-25-1

This compound was prepared from compound 8 in three steps without purifying the intermediate acid and acid chloride. n-BuLi (2.5 M in THF, 0.87 mL, 2.18 mmol) was added drop wise to a stirred solution of 8 (420 mg, 1.82 mmol) in THF (10 mL) at -78 C under N2 atmosphere. After 30 min CO2 gas was passed through the solution during 45 min of time and the mixture was allowed to warm up to room temperature. THF was removed in vacuum and the mixture was treated with saturated NaHCO3 solution (30 mL). The water layer was washed with ethyl acetate (2*15 mL) and then acidified with conc. HCl. The mixture was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4), filtered and concentrated to get the acid 10 (320 mg). Without further purification it was dissolved in CH2Cl2 (10 mL) under N2 atmosphere, DMF (one drop) and oxalyl chloride (0.23 mL, 2.6 mmol) were added. The mixture was stirred for 3 h at room temperature and then the solvent was removed in vacuum to yield the corresponding acid chloride, which was again directly used for the next reaction without further purification. A solution of compound 1114 (514 mg, 2.45 mmol) in THF (7 mL) was added at -78 C to a freshly prepared solution of LDA, prepared from n-BuLi (2.5 M in THF, 1.3 mL, 3.26 mmol) and i-Pr2NH (0.45 mL, 3.26 mmol) in THF (5 mL) at 0 C under N2 atmosphere. The thus produced yellowish anion was stirred at -78 C for 45 min and then a solution of crude acid chloride, prepared earlier, in THF (10 mL) was added drop wise. The reaction was stirred at the same temperature for another 45 min and then at room temperature for 4 h. 10% HCl (10 mL) was added to quench the reaction, THF was removed in vacuum and the water layer was extracted with ethyl acetate (2*50 mL). The organic layer was washed with water (2*20 mL), brine (20 mL), dried (Na2SO4) and concentrated. The crude product was purified by silica gel column chromatography to get 13 (480 mg, 68% in three steps) as yellowish oily compound. Rf 0.5 (1:1 ethyl acetate:hexane); numax (CHCl3) cm-1 1732, 1659, 1608, 1508, 1463, 1211, 1029; 1H NMR (CDCl3, 500MHz): delta 7.71 (s, 1H, C6?-H), 7.01 (d, 1H, J=8.5Hz, C6?-H), 6.43 (s, 1H, C3?-H), 6.41 (d, 1H, J=8.5Hz, C5?-H), 6.28 (s, 1H, C3?-H), 5.94 (s, 1H, C2-H), 3.82 (s, 3H, OCH3), 3.76 (s, 3H, OCH3), 3.75 (s, 3H, OCH3), 3.74 (s, 3H, OCH3), 3.71 (s, 3H, CO2CH3), 2.10 (s, 3H, CH3); 13C NMR (CDCl3, 125MHz): delta 193.1 (C), 171.1 (C), 163.0 (C), 160.3 (C), 159.6 (C), 157.9 (C), 133.1 (CH), 130.1 (CH), 118.9 (C), 118.0 (C), 115.8 (C), 104.1 (CH), 98.4 (CH), 94.1 (CH), 57.2 (CH3), 55.5 (CH3), 55.3 (CH3), 55.2 (CH3), 55.2 (CH3), 52.1 (CH), 15.3 (CH3); HRMS (EI+) m/z 388.1529 ([M]+ C21H24O7, requires 388.1521).

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

Reference:
Article; Pahari, Pallab; Saikia, Ujwal Pratim; Das, Trinath Prasad; Damodaran, Chendil; Rohr, Juergen; Tetrahedron; vol. 72; 23; (2016); p. 3324 – 3334;,
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Application of 609-12-1, 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. 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, This compound has unique chemical properties. The synthetic route is as follows.

[00485] 2-(1’Benzyl’2-methyl-1H-indol-4’yloxy)-3-methyl-butyric acid ethyl ester 7:1-Benzyl-2-methyl-1H-indol-4-ol 3 (0.3 g 1.26 mmole) was dissolved in anhydrous dimethylformamide (20 ml_). To the solution sodium hydride 60% in mineral oil (66 mg 1.65 mmole) was added. The mixture was stirred at room temperature for 1 h. To the mixture ethyl-2-bromoisovalerate (0.344 mL, 1.65 mmole) was added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (300 mL) and washed with H2O (4 x 100 mL) and brine (1 x 100 mL). The organic layer was separated, dried with magnesium sulfate and concentrated. The residue was purified by column chromatography (10:1 Hexane:EtOAc) to afford a 1 :1 mixture of 7:ethyl-2-bromoisovalerate. Further purification by column chromatography (10:1 Hexane.epsilontOAc) afforded 7 (0.09 g, 19 %) as a yellow oil.

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

Reference:
Patent; ILYPSA, INC.; WO2007/56279; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics