Month: May 2021

Electric Literature of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of (-R NH (4.74 mL, 33.2 mmol) in THF (40 mL) at 0C was added n-BuLi (13.3 mL of a 2.5M solution in hexanes, 33.2 mmol) portionwise. The LDA solution was stirred for 15 min at 0C, then was warmed to RT, and stirred for 30 min at RT, then was cooled to-78C. Tert-butyl cyclopropanecarboxylate (3.78 g, 26.6 mmol) was added dropwise over 10 min. The reaction was stirred at -78C for 2 h, after which l-bromopropane (4.84 mL, 53.2 mmol) was added dropwise over 20 min. The reaction was allowed to slowly warm to RT and stirred overnight at RT, then was quenched with satd aq. NH4Cl and extracted with EtOAc (2x). The combined organic extracts were washed with brine, dried (MgSCri), and concentrated in vacuo. The residue was distilled under reduced pressure (20 torr, BP = 95C) to give the title compound (2.99 g, 61 % yield) as an oil. NMR (500 MHz, CDCb) d 1.48 (m, 4H), 1.45 (s, 9H), 1.12 (m, 2H), 0.92 (m, 3H), 0.61 (m, 2H).

The synthetic route of tert-Butyl cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHENG, Peter Tai Wah; KALTENBACH III, Robert F.; SHI, Jun; SHI, Yan; ZHANG, Hao; (0 pag.)WO2020/60915; (2020); 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. 17229-14-0, name is Ethyl 2-(2-chloroethoxy)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C6H11ClO3

EXAMPLE 58 Ethyl (S)-2-(1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepin-2-yl)ethoxyacetate 32.48 g of (S)-1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine (prepared as described in Preparation 3), 22.7 g of ethyl 2-chloroethoxyacetate, 48.9 g of sodium carbonate and 0.79 g of sodium iodide were added to 340 ml of 4-methyl-2-pentanone, and the mixture was heated under reflux for 16 hours. At the end of this time, it was cooled to room temperature and was filtered using a Celite filter aid, and the filtrate was concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel eluted with a 1:1 by volume mixture of ethyl acetate and hexane, to give 44.85 g (yield 91%) of the title compound as a pale yellow oil.

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; Sankyo Company, Limited; US5362725; (1994); A;; ; Patent; Sankyo Company, Limited; US5476848; (1995); A;,
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Some common heterocyclic compound, 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, molecular formula is C8H7Cl2NO2, 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 4-amino-3,5-dichlorobenzoate

EXAMPLE 5 1-Acetyl-2-(4-carbomethoxy-2,6-dichlorophenylimino)imidazolidine Methyl-4-amino-3,5-dichlorobenzoate (16.8 g, 31 mmole), 1-acetyl-2-imidazolidone (4.3 g, 33.5 mmole) in phosphoryl chloride (44 ml) were stirred at 50 C. for 3 days. After cooling the phosphoryl chloride was evaporated to give an oily residue. Iced water was added to the residue which was then basified with aqueous sodium hydroxide. The mixture was extracted with methylene chloride which was then washed with water, dried (magnesium sulphate) and evaporated to give a creamy solid. This solid was recrystallized from toluene to give the title compound (7.7 g) mp 188-189 C. Analysis calculated for C13 H13 Cl2 N3 O3: Theory: C, 47.30; H, 3.97; N, 12.73. Found: C, 47.34; H, 3.88; N, 12.60.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41727-48-4, its application will become more common.

Reference:
Patent; Beecham Group p.l.c.; US4505926; (1985); A;,
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These common heterocyclic compound, 13031-39-5, name is 3-Chlorophenyl 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. Formula: C8H7ClO2

i) 4-Chloro-2-hydroxyacetophenone In a 500 mL of round bottom flask purged with argon was placed 26.00 g (0.153 mol) of 3-acetoxychlorobenzene, cooled with ice bath. Then 30.00 g (0.225 mol) of AlCl3 was added in portions. The resulting mixture was heated to 140 C. for 2 h (caution: vigorous evolution of gas) and then cooled to 0 C. treated with 15 mL of conc. HCl in 100 mL of ice water, extracted with EtOAc (3×300 mL). The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent gave 24.00 g (92%) of the title compound as a light yellow liquid: 1H NMR (250 MHz, CDCl3) d 10.7 (s, 1H), 7.65 (d, J=8.6 Hz, 1H), 6.98 (d, J=1.8 Hz, 1H), 6.87 (dd, J=1.8, 8.6 Hz, 1H), 2.61 (s, 3H).

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

Reference:
Patent; SmithKline Beecham Corporation; US6353116; (2002); B1;,
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Synthetic Route of 33577-99-0, These common heterocyclic compound, 33577-99-0, name is Methyl 2-ethynylbenzoate, 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.

General procedure: Appropriate halogenoarene (1 eq) was dissolved in triethylamine(TEA) and the solution was cooled to 0 C. Then a traceamount of copper iodide and bis(triphenylphosphine)palladium(II)dichloride, Pd[(C6H5)3P]2Cl2 as catalysts were added. After a fewminutes acetylene derivative (2 eq) was added. The reactionmixture was stirred for about 9 h and then was filtered, extracted with ethyl acetate andwashed withwater. Combined organic layerswas dried over anhydrous magnesium sulfate, filtered and thesolvent was evaporated. The pure products 1a-2a were isolated by:crystallization from a mixture of ethyl acetate and petroleum ether(1a) and ethyl acetate (2a) or by column chromatography on silicagel (petroleum ether/ethyl acetate 20:1 (v/v) (5b)).

Statistics shows that Methyl 2-ethynylbenzoate is playing an increasingly important role. we look forward to future research findings about 33577-99-0.

Reference:
Article; Szyszkowska, Ma?gorzata; Czaplewski, Cezary; Wiczk, Wies?aw; Journal of Molecular Structure; vol. 1138; (2017); p. 81 – 89;,
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Related Products of 58304-65-7,Some common heterocyclic compound, 58304-65-7, name is 1-Chloro-2-methylpropyl propionate, molecular formula is C7H13ClO2, 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 32 2-Butyl-6-(butyloxy)-3-[[2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl]oxy]-5-quinoxalinecarboxylic acid, 2-methyl-1-(1-oxopropoxy)propyl ester A mixture of Example 24 (0.51 g, 0.95 mmol) and silver oxide (1.50 g, 6.5 mmol) in tetrahydrofuran (5 mL) was stirred in the presence of molecular sieves (1.5 g, 4 A powder) at 65 C. for 5 minutes. Propanoic acid, 1-chloro-2-methylpropyl ester (0.4 mL) was then added and the resulting mixture was stirred at 65 C. for 4 hours. It was cooled to 0 C., acidified with 1N aqueous hydrochloric acid (15 mL) and filtered through a Celite pad, and the pad was washed with tetrahydrofuran (50 mL). The combined filtrate solution was washed with brine, dried over sodium sulfate and concentrated. The crude product, which contained a dialkylated analogue, was dissolved in methanol (10 mL) and 5% aqueous sodium hydrogen carbonate (2.0 mL), and the mixture was stirred at room temperature for 1 hour. Solid sodium hydrogen carbonate (0.5 g) was added and the mixture was stirred at room temperature for 5 hours more. It was acidified with 1N aqueous hydrochloric acid and concentrated. The residue was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel eluding with hexane/ethyl acetate/acetic acid (2:1:0.01) to afford Example 32 (0.36 g, 57%) as an oil and the dialkylated compound (0.41 g), contaminated with small amount of impurities. 1 H NMR (CDCl3) delta7.97 (d, J=9.4 Hz, 1H), 7.95 (d, J=7.0 Hz, 1H), 7.59-7.46 (m, 3H), 7.30 (d, J=9.4 Hz, 1H), 7.17 (m, 4H), 6.92 (d, J=5.3 Hz, 1H), 4.15 (m, 2H), 3.06 (t, J=7.6 Hz, 2H), 2.30 (q, J=7.0 Hz, 2H), 2.02 (ot, J=5.1 Hz, 1H), 1.81 (m, 4H), 1.51 (m, 4H), 1.07-0.88 (m, 15H); 13 C NMR (CDCl3) delta173.1, 164.3, 156.1, 155.7, 152.4, 149.3, 140.6, 135.8, 133.9, 130.9, 130.8, 130.6, 130.5, 129.9, 127.8, 123.0, 121.6, 116.9, 114.0, 93.3, 69.1, 33.0, 31.5, 31.1, 29.7, 27.3, 22.5, 18.9, 16.4, 15.9, 13.8, 13.6, 8.7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-2-methylpropyl propionate, its application will become more common.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5380719; (1995); A;,
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Related Products of 117324-58-0, 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. 117324-58-0 name is Methyl 2-amino-5-(trifluoromethyl)benzoate, 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.

To a solution of compound 13a (0.92 g, 4.2 mmol) and Boc 2O (3.17 g, 14.7 mmol) in THF (15 mL) was added DMAP (256 mg, 2.1 mmol) at 26-32C. The reaction was stirred at 26-32C for 4 h. The reaction solution was concentrated in vacuum to give the crude residue, which was purified by column chromatography on silica gel (0-10%EtOAc in petroleum ether) to afford the desired product compound 13b (1.43 g, 81.2% yield) as an off-white solid. LCMS: Rt = 1.078 min in 5-95AB_220&254. lcm chromatography (MERCK RP-18e 25-2mm), MS (ESI) m/z= 442.1 [M+23] +. 1H NMR (400MHz, CDCl 3) delta 8.28 (d, J=1.6 Hz, 1H), 7.95 (dd, J=2.0, 8.4 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H), 3.93 (s, 3 H), 1.36 (s, 18 H).

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

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
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Electric Literature of 1415920-00-1, 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. 1415920-00-1 name is Ethyl 4-amino-3,5-difluorobenzoate, 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.

To a solution of ethyl 4-amino-3,5-difluorobenzoate (i-27b) (1 g, 4.98 mmol), t-BuONO (3769 mg, 7.46 mmol) in20 mL CH3CN at room temperature was added CuBr2 (1.66 g, 7.46 mmol). The mixture wasstirred at room temperature for 1 hour, diluted with water (40 mL), and extracted with EtOAc(40 mL*2). The combined organic layers were washed with brine, dried over Na2SO4,filtered and concentrated. The residue was purified by column chromatography on silica gel(PE/EA = 100/1 to 20/1) to afford the title compound (0.9 g, 68 % yield). LCMS (ESI) calc?dfor C9H7BrF2O2 [M+H]: 265, found: 265.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-amino-3,5-difluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan; WO2014/28589; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1462-12-0, name is Diethyl 2-ethylidenemalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1462-12-0, Formula: C9H14O4

General procedure: In the following examples, if, Ig, Ih, and Ii are radical precursors, respectively, and reacted with Michael acceptor II to obtain an addition product III.Using the optimal reaction conditions:Base K2HPO4, photocatalyst [Ir(ppy)2(dtbbpy)]PF6 (1 mol%), solvent acetone (concentration: 0.2 M), light source 34W blue LED bulb, reaction temperature 40 C.

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

Reference:
Patent; Sichuan University; Song Hao; Qin Yong; Xue Fei; Liu Xiaoyu; Zhang Dan; Wang Falu; Liu Jiazhen; Di Jiamei; Liao Qi; Lu Huifang; Zhu Min; He Liping; (29 pag.)CN108456156; (2018); A;,
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Related Products of 57486-69-8,Some common heterocyclic compound, 57486-69-8, name is Methyl 2-(2-bromophenyl)acetate, molecular formula is C9H9BrO2, 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-(4-Chloro-phenoxy)-phenyl]-acetic acid (IX) Methyl 2-bromophenylacetate (47.0 grams 216.3 mmol) and 4-chloro-phenol (27.8 grams, 215.8 mmol) were dissolved in dioxane (790 ml) while warming to 50 C. To the resulting solution were added, under stirring in an inert nitrogen atmosphere, cesium carbonate (141 grams, 432.2 mmol) and copper(l) chloride (18.56 g, 86.2 mmol). Finally, N,N-dimethylglycine (4.46 grams, 43.2 mmol) was added to the green suspension. The reaction mixture was heated at 110 C. (reflux temperature) for 4 days while stirring. The reaction mixture was filtered over dicalite, which was washed with dioxane (40 ml). The dioxane was removed in vacuo to leave a brownish oil. Ethyl acetate (100 ml) was added to the oil and the pH of the resulting mixture was adjusted to 1 by addition of 1 M HCl (300 ml). The organic phase was washed with saturated brine (300 ml), dried on magnesium sulphate and then concentrated under vacuum to yield 57.2 grams (206 mmol; 95 %) of 2-(4-chloro-phenoxy)-phenyl]-acetic acid methyl ester as a brown oil.

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-(2-bromophenyl)acetate, its application will become more common.

Reference:
Patent; Organon Ireland Ltd.; Pfizer Inc.; US2006/229352; (2006); A1;,
Ester – Wikipedia,
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