Tag: M.W=200-300

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. 83-27-2, name is Diethyl 2-(sec-butyl)malonate, A new synthetic method of this compound is introduced below., name: Diethyl 2-(sec-butyl)malonate

A. 3-sec-Butyl-6-fluoro-4-hydroxyl-2(1H)-quinolinone The title compound was prepared from 4-fluoroaniline (10 g, 80 mmol) and diethyl sec-butylmalonate by the method used in Example 1. Reaction time was 5 d. MS (ES+): m/z 236.0 (M+H); 1H NMR (DMSO-d6) delta 11.2 (bs, 1H, OH), 9.95 (bs, 1H, NH), 7.60 (d, 1H, ArH), 7.31-7.20 (m, 2H, ArH), 3.13 (m, 1H, CH), 1.9 (m, 1H, CH), 1.6 (m, 1H, CH), 1.2 (d, 3H, CH3), 0.7 (m, 3H, CH3).

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; Andrews,III, Clarence Webster; Freeman, George Andrew; Hopkins, Andrew Lee; US2003/69271; (2003); A1;,
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Related Products of 1732-09-8, The chemical industry reduces the impact on the environment during synthesis 1732-09-8, name is Dimethyl octanedioate, I believe this compound will play a more active role in future production and life.

Adipinsuredimethylester wurde kontinuierlich in Rieselfahrweise mit Rckfhrung (Verhltnis Zulauf / Rckfhrung = 10/1) bei einer Belastung von 0,5 kg/(l*h), einem Druck von 240 bar und Reaktionstemperaturen von 200 C bzw. 220 C in einem senkrechten Rohrreaktor, der mit 200 ml des Vergleichskatalysators gefllt war, hydriert. Die Versuchsdauer betrug insgesamt 14 Tage. GC-analytisch wurde im Reaktoraustrag bei 200 C bzw. 220 C Esterumstze von 92% bzw. 96%, Hexandiol-Anteile von 48 % bzw. 58 % und Methanol-Gehalte von 25 % bzw, 28 % detektiert. Nach Ausbau war der Katalysator zwar noch voll erhalten, die mechanische Stabilitt hatte aber deutlich nachgelassen. Seitendruckfestigkeit und Abrieb sind in Tabelle 1 zusammengestellt. Die Versuchsergebnisse sind in Tabelle 2 zusammengefat.

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 octanedioate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; EP1218326; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-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. Computed Properties of C9H9BrO2

Step (vi); Methyl 3-cyanophenylacetate; [Show Image] The compound 10.65g (46.5mmol) obtained in step (v) and zinc cyanide 3.44g (29.3mmol) were dissolved in DMF 120ml and stirred at room temperature for 30 minutes under an atmosphere of nitrogen. Thereto was added tetrakis(triphenylphosphine)palladium 2.15g (1.86mmol) and the mixture was refluxed at 90C for 3 hours under an atmosphere of nitrogen. After lowering the temperature and filtration over Celite, the filtrate was concentrated. The residue was extracted with ethyl acetate, washed with 2N aqueous ammonia (50ml) and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography (SiO2 200g, eluent : Hexane/EtOAc=9/ 1) to give the object compound 4.28g as a pale yellow oil. Yield 53% 1H NMR (CDCl3) delta 7.52 (4H, m), 3.72 (3H, s), 3.67 (2H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150529-73-0, its application will become more common.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1939202; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 609-12-1,Some common heterocyclic compound, 609-12-1, name is Ethyl 2-bromo-3-methylbutanoate, molecular formula is C7H13BrO2, 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: Benzenesulfonamide (1.2mmol), ethyl alpha-bromophenylacetate or ethyl pheny-lacetate (2.4mmol), and toluene (4mL)werecombinedinasealedtubeequippedwith astirbar.Themixturewasstirredat50Cfor10min,TiCl4 (1.8 mmol) was added, andthereactionmixturewasheatedto115C.Afteravariableperiodoftimethe mixturewasdilutedwithH2O (10mL)toremovetheexcessofTiCl4, filtered,andextracted withAcOEt(3¡Á15mL). The combined organic layers were dried over anhydrous Na2SO4 and thesolventwasevaporatedinvacuo.Crudecompoundswere purified by flash column chromatography (silicagel;cyclohexane=AcOEt 8:2). 2-Bromo-3-methyl-N-(phenylsulfonyl)butanamide (4a). Yellowish oil, 98% yield. IR (KBr)3590, 3530, 3236, 2970, 2876, 1719, 1450, 1352, 1174, 1085, 865 cm-1; 1H NMR (CDCl3) d 0.93(d, 3H, J 6.3 Hz, CH3), 0.96 (d, 3H, J 6.9 Hz, CH3), 2.21 (octuplet, 1H, CH3CHCH3), 4.10 (d, 1H, J5.7 Hz, CHBr), 7.56 (t, 2H, J 8.1 Hz, CH Ar), 7.67 (t, 1H, J 7.8 Hz, CH Ar), 8.07 (d, 2H, J 7.2 Hz,CH Ar), 8.91 (broad s, 1H, NH); 13C NMR (CDCl3) d 18.8 (CH3), 20.2 (CH3), 32.5 (CH3CHCH3),58.2 (CHBr), 128.5 and 129.0 (CH Ar), 134.3 (CS Ar), 137.7 (CH Ar), 166.0 (CONH); Anal calcdfor C11H14BrNO3S: C 41.26; H 4.41; N 4.37; found C 41.23; H 4.43; N 4.36 %.

The synthetic route of 609-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ammazzalorso, Alessandra; Tricca, Maria Luisa; Bruno, Isabella; De Filippis, Barbara; Di Matteo, Mauro; Fantacuzzi, Marialuigia; Giampietro, Letizia; Maccallini, Cristina; Mollica, Adriano; Amoroso, Rosa; Synthetic Communications; vol. 45; 22; (2015); p. 2546 – 2554;,
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Adding a certain compound to certain chemical reactions, such as: 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, 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 79669-50-4, Application In Synthesis of methyl 5-bromo-2-methyl-benzoate

To a I OL five necked flask fitted with condenser, stirrer bar, N2 inlet and bubbler was added methyl-5-bromo-2methylbenzoate (500.0 g, 2.18 mol, 1.0 eq.) and Nbromosuccinimide (Fluorochem, 388.5 g, 2.18 mol, 1.0 eq.)to a stirring solution of 1,2-dichloroethane (1.9 L). Themixture was heated to 90 C (oil bath). Azobisisobutyronitrile (5.0 g, 0.03 mol, 0.014 eq.) was dissolved into DCE (100 mL) and 20 mL was added into a dropping funnel. This was added slowly when the reaction mixture reached 85 C. When the violent reflux and foaming ceased, the remaining 80 mL was added in one portion to the reaction mixture and left to stir at 90 C for 1 hr. NMR showed the reaction to be complete with around 11% of starting material stillremaining. The reaction mixture was then cooled to room temperature using cardice in the oil bath and once the internal temperature had fallen to -30C, the reaction mixture was quenched with water (2.OL). After 5 minutes, two identical reaction mixtures were combined, transferred to a separating funnel and the organic layer was collected. The aqueous layer was extracted again using DCM (2 x 2.OL). All the organic layers were combined and washed with water (2L) andbrine (2L), dried with MgSO4, filtered and concentrated under vacuo to give an orange liquid (1.397 kg, 104%, from 2 x 500g runs).

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 5-bromo-2-methyl-benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; READER, Michael; WILSHER, Nicola Elizabeth; SAUNDERS, Mark Henry; BAGULEY, Paul Anthony; LINDLEY, Colin Thomas; MELLING, Robert Craig; ADAMCZYK, Bozena Ewa; SCARATI, Mirka; (117 pag.)WO2018/193410; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

Related Products of 41841-16-1,Some common heterocyclic compound, 41841-16-1, name is Methyl 2-(4-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.

To a solution of diisopropylamine (2.2 g, 21.8 mmol) in THF (20 mL), was added n-BuLi in hexane (13.7 mL, 21.8 mmol) at -78 C, stirred for 1 hour at -78 C and 12 hours at RT, again cooled to -78 C, added a solution of methyl 2-(4-bromophenyl) acetate (2 g, 8.7 mmol) in THF (10 mL) followed by methyl iodide (1.61 g, 11.35 mmol) at -78 C. The reaction mixture was stirred at -78 C for 1 h and 12 h at room temperature. The reaction mass was quenched with saturated aq. ammonium chloride solution (10 mL) and extracted with ethyl acetate (2 x 10 mL). The combined organic layers were washed with water (2 x 15 mL), dried over sodium sulphate and then concentrated under reduced pressure. The residue was purified using column chromatography (silica gel, 2 % ethyl acetate in hexane) to afford Methyl 2-(4-bromophenyl)propanoate (38) as pale yellow liquid (1.4 g, 66 %); 1H NMR (400 MHz, CDCl3) delta 7.44 (d, J = 8.4 Hz, 2H), 7.18 (d, J = 8.4 Hz, 2H), 3.67 (t, J = 7.6 Hz, 3H), 3.64 (s, 1H), 1.48 (d, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 174.48, 139.49, 131.73, 129.27, 121.10, 52.14, 44.88, 18.47; IR (KBr) numax 2980.61, 2951.96, 1736.40 cm-1; ESI-MS: m/z 242.9 (M+H)+.

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

Reference:
Article; Bhatthula, Bharath kumar goud; Kanchani, Janardhan reddy; Arava, Veera reddy; Subha; Tetrahedron; vol. 75; 7; (2019); p. 874 – 887;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

55954-23-9, name is Methyl 2,4-dichlorophenylacetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: Methyl 2,4-dichlorophenylacetate

Methyl 2-(2,4-dichlorophenyl) acetate (10.6 g, 48.4 mmol) was dissolved in THF (100 mL), and sodium hydride (55% w/w, 2.53 g, 58.1 mmol) was added little by little thereto under ice-cooling, followed by stirring for 10 minutes. tert-Butyl dicarbonate (11.1 g, 50.8 mmol) was added to the reaction solution at the same temperature, and the temperature was slowly raised to room temperature, followed by stirring for 23 hours. Thereafter, tetrabutyl ammonium chloride (4.03 g, 14.5 mmol) was added to the reaction solution, followed by stirring for 20 hours. Sodium hydride (55% w/w, 2.53 g, 58.1 mmol) was added little by little to the reaction solution under ice-cooling, followed by refluxing for 23 hours. After the reaction was completed, the reaction solution was added little by little to saturated ammonium chloride aqueous solution (150 mL) under ice-cooling, and the resultant product was extracted with ethyl acetate (100 mL*2, 50 mL*1). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, whereby a brown oily crude product (13.4 g) was obtained. This was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), whereby tert-butyl 2-(2,4-dichlorophenyl) malonate (5.41 g, yield: 35%) was obtained as a yellow oily material. 1H-NMR (400 MHz, CDCl3): delta1.46 (s, 9H), 3.67 (s, 3H), 5.09 (s, 1H), 7.27-7.44 (m, 3H).

The synthetic route of 55954-23-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAKEN PHARMACEUTICAL CO., LTD.; SAGAMI CHEMICAL RESEARCH INSTITUTE; KOBAYASHI, Osamu; NIIKURA, Naoko; INOUE, Tomoko; MIZUTA, Satoshi; TAKATSUNA, Reiko; HIRAI, Kenji; SHIROUZU, Kentaro; OBATA, Miyoo; (183 pag.)US2016/24110; (2016); 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. 55666-43-8, name is tert-Butyl 3-bromopropanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H13BrO2

REFERENCE EXAMPLE 13 4,5-Dichloro-2-{2-(t-butoxycarbonyl)ethyl}-3(2H) pyridazinone STR20 In the same manner as in Reference Example 10, a mixture comprising 19.3 g of 4,5-dichloro-3(2H) pyridazinone, 29.4 g of 2-(t-butoxycarbonyl)ethylbromide, 19.3 g of potassium carbonate, 1.75 g of sodium iodide and 60 ml of dimethylformamide, was reacted, and the oily substance thus obtained was purified by silica gel column chromatography (developer: benzene:ethyl acetate=10:1, v/v) to obtain 8.1 g of the above identified compound as a pale yellow oily substance.

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 55666-43-8.

Reference:
Patent; Nissan Chemical Industries Ltd.; US4892947; (1990); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 25542-62-5, 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. 25542-62-5 name is Ethyl 6-bromohexanoate, 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.

Step 2. Synthesis of ethyl 6-(6-fluor-2,2-dimethyl-4-oxo-l ,2,3,4-tetrahydrocarbazol-9-yl) hexanoate [Foumula 1-3]6-fluoro-2,2-dimethyl-2,3-dihydro-lH-carbazol-4(9H)-on [formula 1-2] (0.1 g, 0.43 mmol) was dissolved in DMF (20 mL), and NaH(0.015 g, 0.645 mmol) was added and stirred for 10 minutes. Then, ethyl 6-bromohexanoate (0.096 g, 0.43 mmol) was added and stirred at 60C for 12 hours. After the completion of the reaction, DMF was distilled out under reduced pressure, the reaction mixture was extracted with ethyl acetate and saturated NaHC03 aqueous solution, the organic layer was washed with brine, dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. Residue was purified by column chromatography (Si02; hexane/ethylacetate, 3/1 ) to yield the title compound (0.18 g, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 6-bromohexanoate, and friends who are interested can also refer to it.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; KIM, Yuntae; LEE, Changsik; YANG, Hyun-mo; CHOI, Hojin; MIN, Jaeki; KIM, Soyoung; KIM, Dal-Hyun; HA, Nina; KIM, Jung-Min; LIM, Hyojin; KO, Eunhee; WO2013/62344; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 24398-88-7, name is Ethyl 3-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 3-bromobenzoate

Ethyl 3-bromobenzoate (0.500 g, 2.18 mmol) was dissolved in CH3CN ( 8.70 ml). Triethylamine (1.53 ml, 10.9 mmol) was added followed by 3,3-dimethylbut-l-yne (0.27 g, 3.27 mmol). With stirring Pd(PPh3)4 (0.25 g, 0.21 mmol) and CuI (0.083 g, 0.436 mmol) were added and the reaction was warmed to 60 C for 4 h. The reaction was then diluted with EtOAc (~ 50 ml), filtered through a pad of SiO2, and concentrated in vacuo. The crude product was purified on 40 g SiO2 using hexanes-EtOAc (10:1) as eluent giving 0.45 g of the title compound as a colourless oil (91 %); m/z 231.

The synthetic route of 24398-88-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/24834; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics