Author: Jessica.F

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,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 3681-71-8, name is cis-3-Hexenyl acetate, molecular formula is C8H14O2, 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. Application In Synthesis of cis-3-Hexenyl acetate

EXAMPLE 8 Preparation of cis 3-hexen-1-yl 3-(beta-naphthyl)-3-oxo-propionate Lithium diisopropylamide (133.0 mL of a 2.0 M solution, 0.266 mol) is placed into a 500 mL three-necked round-bottomed flask fitted with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 C. cis 3-Hexenyl acetate (17.80 g, 0.125 mol) is dissolved in THF (10 mL) and the resulting solution added to the flask over 45 min. Once addition is complete, the mixture is stirred for an additional 15 min. before being treated with a solution of 2-naphthoyl chloride (22.51 g, 0.118 mol) dissolved in THF (30 mL) over 30 min. The mixture is warmed to -20 C. and stirred at that temperature for 18 h. After warming to 0 C., the mixture is quenched with 20% HCl (70 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2*100 mL), water (2*150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to give an orange/red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether) to yield a colorless oil having 1 H and 13 C NMR spectra consistent with the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3681-71-8, its application will become more common.

Reference:
Patent; The Procter & Gamble Company; US6100233; (2000); A;,
Ester – Wikipedia,
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Related Products of 87808-49-9, The chemical industry reduces the impact on the environment during synthesis 87808-49-9, name is Methyl 2-bromo-4-methylbenzoate, I believe this compound will play a more active role in future production and life.

NBS (8.53 g, 48 mmol) was added to a solution of methyl 2-bromo-4- methylbenzoate (10.4 g, 45.6 mmol) in CCl4 (400 ml), followed by benzyol peroxide (441 mg, 1.82 mmol). The reaction mixture was then heated to reflux and after 2 h, the reaction mix became colorless. The mixture was allowed to cool to room temperature and before it was filtered. The filtrate was concentrated to give 12 g of crude material which was purified by column chromatography (440 g silica gel 60, 230-400 mesh, 10 then 20 % CH2Cl2/hexane) to give methyl 2-bromo-4-(bromomethyl)benzoate (5.07 g, 36 %) as a white solid. MS (m/z) 307.3(M+H+).

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, Methyl 2-bromo-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.; WO2008/124575; (2008); A1;,
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Application of 2967-93-3,Some common heterocyclic compound, 2967-93-3, name is Methyl 2-fluoro-5-methylbenzoate, molecular formula is C9H9FO2, 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 solution of methyl 2-fluoro-5-methylbenzoate (6.72 g, 40 mmol)Was added to the reaction flask, CC14 (1 OOmL) was added, NBS (7.47 g, 42 mmol) was added, AlphaIBN (1.29 g, 8 mmol)(100 mL) was added, washed with saturated NaCl (50 mL X3), dried over anhydrous magnesium sulfate, column chromatography (EpsilonAlpha: Rho = 1: 150), and the reaction mixture was heated to reflux. Afforded 6.4 g of white solid in 65% yield.

The synthetic route of 2967-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Zhou Jie; Ji Ming; Yao Haiping; Zhou Qin; (57 pag.)CN107098886; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, 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 18014-00-1, HPLC of Formula: C10H8Br2O4

2.5 g (10 mmol) of N, N-dibutylbenzene-4-boronic acid were dissolved in 30 ml of tetrahydrofuran, Then 2 ml of water was added, 2.12 g (20 mmol) of sodium carbonate, 1.05 g (3 mmol) of dimethyl 2,5-dibromoterephthalate, 120 mg of tetraphenylphosphine palladium, Reaction under nitrogen for 12 hours; After the reaction is completed, Add 20ml of water to extract. Separate the organic phase, The aqueous phase is extracted three times with 20 dichloromethane. The combined organic phase, Drying over anhydrous sodium sulfate. Evaporate the methylene chloride, Column chromatography (petroleum ether: dichloromethane = 5: 1), Have a light yellow solid is the product, See formula V.

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, Dimethyl 2,5-dibromoterephthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lanzhou University; Zhang Haoli; Fan Zhiping; Xu Zhuguo; Shi Zifa; (14 pag.)CN105367451; (2017); B;,
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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. 573-20-6, name is 2-Methylnaphthalene-1,4-diyl diacetate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 573-20-6

2-methyl- 1 ,4-naphthohydroquinone diacetate (3) (23.3 g) were in methanol (116.5 g) and water (11.6 g). Di-isopropylamine (9.04 g) was added and stirred at 20-25C. When the reaction was complete, the mixture was quenched with HCl(aq) and then extracted with ethyl acetate. The organic layer was washed with brine for twice. It was concentrated under reduce pressure and the crude was re-crystallized with ethyl acetate (35 g) and Heptane (116 g), thereby obtaining 9.21 g the title compound. (Yield: 69.3%, HPLC purity: 99.9%).

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 573-20-6.

Reference:
Patent; SUNNY PHARMTECH INC. THAIWAN; Tian, Jian He; Pang, Ju yi; Xu, Nai Xuan; (29 pag.)TW2016/15603; (2016); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics