Tag: M.W=200-300

110661-91-1, A common compound: 110661-91-1, name is tert-Butyl 4-bromobutanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

To a solution of 3-mercapto-5-trifluoromethyl-benzoic acid methyl ester (990 mg, 4.19 mmol) in acetonitrile (25 mL) were added N,N-diisopropylethylamine (1.08 g, 1.46 mL, 8.38 mmol) and tert-butyl 4-bromobutanoate (935 mg, 4.19 mmol, CAS RN 110611-91-1). The clear yellow solution was stirred at room temperature for 2.5 hours and then poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 50 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow liquid (1.27 g, 80%). MS (ESI+): m/z=379 ([M+]).

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 4-bromobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; Dehmlow, Henrietta; Erickson, Shawn David; Mattei, Patrizio; Richter, Hans; US2013/267519; (2013); 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. 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., 14062-25-0

Synthesis of compound 166.1. To a solution of ethyl 161.1 (5.0g, 20.6 mmol, l .Oeq) in CH2CI2 (50 mL) was added preraformaldehyde (0.938g, 24.69mmol, 1.2eq) followed by tetrabutylammonium chloride (0.571g, 2.05mmol, O. leq), and K2CO3 (6.2g, 45.26mmol, 2.2eq). The reaction was stirred at 60 C 3h. The reaction mixture was quenched with ice cold water and product was extracted with CH2CI2 (50mL x 2). Organic layer were combined and dried over sodium sulphate and concentrated under reduced pressure to obtain 166.1 (2.5g, 47.65%). MS (ES):256.4 m/z [M+H]+.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 24398-88-7, name is Ethyl 3-bromobenzoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 24398-88-7

The zinc reagent 2c was prepared according to TP1 from methyl3-bromo-4-(((trifluoromethyl)sulfonyl)oxy)benzoate (1c,7.26 g, 20 mmol), Zn-powder (3.92 g, 60 mmol) and InCl3(0.33 g, 1.5 mmol). The reaction mixture was stirred in DMPU(20 mL) at 50 C for 2 h. Iodolysis indicated a yield of 70% bimetallic reagent (14 mmol). The solution containing the zinc reagent was separated from the remaining zinc powder and transferred to a new flask containing a solution of ethyl 3-bromobenzoate (3e, 9.16 g, 40 mmol) and PEPPSI-iPr (0.19 g,0.28 mmol) in THF (20 mL). The reaction mixture was stirred at 50 C for 12 h before being quenched with HCl (2 M, 50 mL). Flash column chromatographical purification on silica gel(pentane/diethyl ether = 4:1) afforded 4e as a colorless oil (3.82 g, 8.83 mmol, 63%).

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, 24398-88-7, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Klatt, Thomas; Bluemke, Tobias D.; Ganiek, Maximilian A.; Knochel, Paul; Synthesis; vol. 46; 3; (2014); p. 290 – 294;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

18066-68-7, 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. 18066-68-7 name is Ethyl 2-(3,4-dimethoxyphenyl)acetate, 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.

(ii) 19.3 g (0.19 mol) of dried isopropylamine was dissolved in 100 ml of anhydrous tetrahydrofuran. The solution was cooled to -60 C. or below in a dry ice/acetone bath, and 120 ml of a solution of 1.6M n-butyllithium in n-hexane was dropwise added thereto at this temperature with stirring. The mixture was stirred for 15 min, and a solution of 40.37 g (0.18 mol) of ethyl 3,4-dimethoxyphenylacetate in 200 ml of anhydrous tetrahydrofuran was dropwise added thereto at the same temperature. After stirring for additional 15 min, a solution of 38.45 g (0.18 mol) of 2-chloro-3-methoxy-beta-nitrostyrene in 400 ml of anhydrous tetrahydrofuran was dropwise added thereto with stirring at such a dropping rate that the temperature of the system did not exceed -50 C. After stirring for 30 min, a small amount of water was added thereto and tetrahydrofuran was distilled off to some extent in vacuo. A 6N hydrochloric acid solution was added to the residue for acidification, and the acidified residue was extracted twice with dichloromethane. The resultant organic phase was washed twice with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography (eluted with a n-hexane/ethyl acetate mixture in a n-hexane to ethyl acetate ratio of 2:1) to prepare 75.1 g of viscous crude ethyl 3-(2-chloro-3-methoxyphenyl)-2-(3,4-dimethoxyphenyl)-4-nitrobutyrate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(3,4-dimethoxyphenyl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Eisai Co., Ltd.; US5444083; (1995); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

154825-97-5, 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. 154825-97-5 name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 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 50 mL two neck flask were added methyl 2- (4-bromophenyl) -2-methylpropionate (689 mg, 2.68 mmol) , (R) -tert-butyl 3-oxohexahydroimidazo [1, 5-a] pyrazine-7 (1H) -carboxylate (630 mg, 2.61mmol) , Pd2(dba)3(180 mg, 0.19 mmol) , 2-di-tert-butylphosphino-2′, 4′, 6′-triisopropylbiphenyl (550 mg, 1.26 mmol) , Cs2CO3(173 mg, 0.53 mmol) and 1, 4-dioxane (25 mL) , the mixture was stirred at 90 for 12 hours. After the reaction was completed, the mixture was cooled to rt and filtered. The filter cake was washed with EtOAc (25 mL) . To the filtrate were added EtOAc (75 mL) and water (50 mL) , the mixture was shaken and separated into layers. The water layer was extracted with ethyl acetate (50 mL) . The combined organic phases were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (V/V) = 1.2/1) to give the title compound as a white solid (200 mg, 17.88%) . MS (ESI, pos. ion) m/z: 440.1 [M+Na]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, and friends who are interested can also refer to it.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; LIU, Xinchang; REN, Qingyun; YAN, Guanghua; GOLDMANN, Siegfried; ZHANG, Yingjun; (253 pag.)WO2019/76310; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, Adding some certain compound to certain chemical reactions, such as: 14062-25-0, name is Ethyl 2-(4-bromophenyl)acetate, 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 14062-25-0.

Ethyl (4-bromophenyl)-acetate (100 g, 411 mmol) Z?-(pinacolato)diboron (125.4 g,493.7 mmol) and potassium acetate (125.4 g, 493.7 mmol) were charged to a 2 L round bottom flask. 1,4-Dioxane (1 L) was added and the mixture was stirred under a nitrogen EPO atmosphere for 15 minutes. [1,1 ‘-Z?w-(Diphenylphosphino)-ferrocene]dichloropalladium(II) CH2Cl2 complex (1:1) (3.36 g, 4.11 mmol) was added and the reaction was heated in an 100 0C oil bath for 2 hours. The reaction was determined complete by analytical HPLC. The solution was concentrated under reduced pressure to remove the dioxane and the residue was dissolved in ethyl acetate. The solution was filtered through a 6 x 4 inch silica gel plug with ethyl acetate (1.5 L) as eluant to give ethyl [4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenylj-acetate (117 g, 98%). 1H NMR (400 MHz, DMSO) delta ppm 7.63 (d, 2H5 J= 8 Hz), 7.27 (d, 2H, J= 8 Hz), 4.07 (q, 2H, J= 7 Hz), 3.68 (s, 2H), 1.28 (s, 12H), 1.16 (t, 3H, J= 7 Hz).

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 14062-25-0.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; WO2006/86609; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 24398-88-7 as follows. 24398-88-7

[00457] To a stirred solution of 1.3 M LHMDS (25 mL, 32.7 mmol) in THF (10 mL) was added EtOAc (1.9 g, 21.8 mmol) at -78 C under inert atmosphere. After being stirred for 15 min, ethyl- 3-bromo benzoate (5 g, 21.8 mmol) was added and stirring was continued for 2 h; progress of the reaction was monitored by TLC. The reaction was quenched with aq. NH4C1 (10 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography eluting with 4% EtOAc/Hexane to afford compound G (4.5 g, 76.9%) as a mixture with its enolic form as a brown oil. 1H NMR (500 MHz, CDCls): delta 8.07 (s, 1H), 7.86 (d, J= 7.5 Hz, 1H), 7.73-7.69 (m, 1H), 7.37 (t, J= 7.0 Hz, 1H), 4.28-4.26 (m, 2H), 3.92 (s, 2H), 1.24 (t, J= 6.2 Hz, 3H). MS (ESI): m/z 298.8 [M-l].

According to the analysis of related databases, 24398-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; COSFORD, Nicholas David, Peter; DHANYA, Raveendra, Panickar; SHEFFLER, Douglas, J.; WO2015/191630; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

110661-91-1, These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, 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.

Step 2: Preparation of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate A flask was charged with 2-hydroxy-4-(trifluoromethyl)benzaldehyde (300 mg, 1.58 mmol, 1.00 equiv), DMF (10 mL), potassium carbonate (654 mg, 4.73 mmol, 3.00 equiv), and tert-butyl 4-bromobutanoate (702 mg, 3.15 mmol, 2.00 equiv). The resulting solution was stirred overnight at 100 C. and quenched with water (30 mL). The resulting solution was extracted with DCM (2*50 mL) and the organic layers were combined, washed with brine (2*30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on a silica gel column with EtOAc/petroleum ether (1/10) to provide 450 mg (86% yield) of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate as a light yellow solid. 1H NMR (300 MHz, Chloroform-d) delta 10.5 (s, 1H), 7.96 (d, J=7.5 Hz, 1H), 7.29-7.33 (m, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.50 (t, J=6.0 Hz, 2H), 2.18-2.25 (m, 2H), 1.49 (s, 9H).

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 110661-91-1.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; (108 pag.)US2018/134674; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 148547-19-7 as follows. 148547-19-7

Step A. Methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate A mixture of methyl 4-bromo-3-methylbenzoate (25.0 g, 110 mmol), o-tolylboronic acid (16.5 g, 120 mmol) and potassium carbonate (50 g, 360 mmol) in dioxane/water (300 mL:200 mL) was purged with nitrogen for 1 hour. [1,-bis(Diphenylphosphino) ferrocene]dichloropalladium [II] (4.5 g, 5.5 mmol) was added. The reaction mixture was heated to 100 C. with vigorous stirring for 3.5 hours, then cooled and filtered through Celitee (Celite Corp., Santa Barbara, Calif.). The cake was washed with ethyl acetate (500 mL). The combined organic phases were washed with 1N sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate, and concentrated in vacuo to afford a dark oil (28.6 g). Purification by flash chromatography using 2% ethyl acetate in hexanes as solvent provided the title compound (24.7 g, 93%) as a pale yellow oil. MS [(+)ESI, m/z]: 241 [M+H]+ HRMS [(+)ESI, m/z]: 241.12205 [M+H]+. Calcd for C16H17O2: 241.12286 Anal. Calcd for C16H16O2: C, 79.97; H, 6.71. Found: C, 79.67; H, 6.61.

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2006/199806; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

23877-12-5, Adding some certain compound to certain chemical reactions, such as: 23877-12-5, name is tert-Butyl 2-bromo-2-methylpropanoate, 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 23877-12-5.

2-Methyl-2-{4-[3-(4-trifluoromethyl-phenyl)-[1,2,4]thiadiazol-5-ylmethylsulfanyl]-phenoxy}-propionic acid tert-butyl ester To a three-necked flask containing NaH (36 mg, 0.90 mmol; 60% in mineral oil) was added a solution of B1 (220 mg, 0.598 mmol) in THF. To the mixture at 40 C. was added tert-butyl 2-bromoisobutyrate (287 mg, 1.29 mmol). After heating at 70 C. for 2 h, more tert-butyl 2-bromoisobutyrate (215 mg, 0.970 mmol) was added and the heating was continued overnight. The mixture was quenched with water (0.1 mL), concentrated, and chromatographed (EtOAc/hexane) to give 81 mg (27%) of B2; 1H NMR (300 MHz, CDCl3) delta 8.35 (d, J=8.2 Hz, 2 H), 7.71 (d, J=8.2 Hz, 2 H), 7.34 (d, J=8.8 Hz, 2 H), 6.78 (d, J=8.7 Hz, 2 H), 4.42 (s, 2 H), 1.55 (s, 6 H), 1.38 (s, 9 H); MS (ES) m/z: 511 (M+H+).

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 23877-12-5.

Reference:
Patent; Kuo, Gee-Hong; Shen, Lan; Wang, Aihua; Zhang, Yan; US2005/96362; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics