Month: December 2020

10259-22-0, 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. 10259-22-0, name is Ethyl 3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step alb: compound A5 (3-(3-methoxyphenyl)-N,N,2-trimethyl-3-oxopropanamide)To 2,2,6,6-tetramethylpiperidine (17.5 g, 125 mmol) in 50 ml dry THF were added dropwise 72 ml (115 mmol) of a n-buthyllithium solution in n-hexane (1.6 M) at -30C. After 30 minutes of stirring, 5.0 g (50 mmol) Nu,Nu-dimethylpropionamide (A1) (dissolved in 50 mL dry THF) were added and the mixture was cooled to -70C and stirred for 1 h at this temperature. 22.5 g (125 mmol) ethyl-3-methoxybenzoate (dissolved in 30 mL dry THF) were slowly added dropwise and the resulting mixture was stirred for another 2 h at -70C. After the mixture had been allowed to warm to RT, it was hydrolyzed by employing a diluted aqueous solution of HCI (36 mL). The mixture was then washed with diethyl ether several times. The combined organic layers were dried over MgS04. The organic solvents were evaporated under reduced pressure and the remaining residue was dried in vacuo. CC (eluent: n-hexane/ethyl acetate (1 :4)) yielded 6.5 g (55%) of A5 in form of a colorless oil.

The synthetic route of 10259-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; BUSCHMANN, Helmut, Heinrich; HOLENZ, Joerg; WO2011/157390; (2011); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 51329-15-8, name is Methyl 3,5-dibromobenzoate, molecular formula is C8H6Br2O2, 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. 51329-15-8

Methyl 5-bromo-2′-chlorobiphenyl-3-carboxylate and methyl 2,2″-dichloro-1,1′:3′,1″-terphenyl-5′-carboxylate Under argon, 60 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to 300 mg (1.02 mmol) of methyl 3,5-dibromobenzoate in 6 ml of dioxane. The mixture was heated to 110 C., and 1.0 ml (2.00 mmol) of 2 M aqueous sodium carbonate solution and 239 mg (1.53 mmol) of 2-chlorophenylboronic acid, dissolved in 1 ml of dioxane, were added successively. The mixture was then stirred at 110 C. for 1 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was separated into the components by preparative HPLC [Method 19]. This gave 142 mg (43% of theory) of methyl 5-bromo-2′-chlorobiphenyl-3-carboxylate (Example 113A) and 166 mg (46% of theory) of methyl 2,2″-dichloro-1,1′:3′,1″-terphenyl-5′-carboxylate (Example 114A) as reaction products. Example 113A GC/MS [Method 20]: Rt=7.50 min; MS [ESIpos]: m/z=324 and 326 (M)+. Example 114A GC/MS [Method 20]: Rt=10.26 min; MS [ESIpos]: m/z=356 and 358 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51329-15-8, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Furstner, Chantal; Keldenich, Joerg; Delbeck, Martina; Kolkhof, Peter; Kretschmer, Axel; Pluschkell, Ingo; Pook, Elisabeth; Schmeck, Carsten; Trubel, Hubert; US2013/190330; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

2033-24-1,Some common heterocyclic compound, 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, molecular formula is C6H8O4, 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.

Meldrum’s adduct (19)2,4,5-Trifluorophenylacetic acid (500.0 gm, 2.63 mol) (18) was suspended in tetrahydrofuran (5.26 vol, 2.63 Ltr) at 25-30C and the reaction mixture was stirred for 10- 15 minutes. To this clear solution, l,r-carbonyldmidazole (1.5 eq, 639.68 gm) was charged in four lots and the reaction mixture was stirred for 2-3 hours at 25-300C. After 2- 3 hours stirring, Meldrum’s acid (1.2 eq, 454.87 gm) was charged and the reaction mixture was heated for 6 hours at 50-550C. After 6 hours heating at 50-55C, the tetrahydrofuran was distilled out completely at 50-55C under reduced pressure to give a dark yellow coloured residue. The dark yellow residue was acidified by using a 1:1 mixture of 35% hydrochloric acid : water (0.5 vol, 250.0 ml) at 0-50C. The product was extracted from the aqueous solution by using dichloromethane (3 x 5.0 vol, 3 x 2.5 Ltr). The combined dichloromethane layers were further washed with water (3 x 10.0 vol, 3 x 5.0 Ltr). After water washing, the dichloromethane was completely distilled under reduced pressure to give a dark yellow fluffy solid. The product was further washed with methanol (2.0 vol, 1.0 Ltr) at 0-50C.Molar Yield: 60-65% (505.0 gm) Chemical Purity: 98-99.5% (as measured by HPLC)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2033-24-1, its application will become more common.

Reference:
Patent; GENERICS [UK] LIMITED; MYLAN INDIA PRIVATE LIMITED; GORE, Vinayak Govind; GADAKAR, Maheshkumar; BHOSLE, Priyanka; SHINDE, Suresh; WO2010/131025; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3196-15-4, A common compound: 3196-15-4, name is Methyl 2-bromobutyrate, 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.

[459] Step 1: methyl 2-{5-nitro-2-[(4-methylbenzoyl)imino]benzo[d]thiazol-3(2H)-yl}butanoate[460] To a stirred solution of 4-methyl-N-(5-nitrobenzo[d]thiazol-2-yl)benzamide (0.96 g, 3.06 mmol) prepared in Preparation 10 in N,N-dimethylformamide (30 mL), were added potassium carbonate (930 mg, 6.73 mmol) and methyl 2-bromobutyrate (0.76 mL, 6.13 mmol). The reaction mixture was stirred at 50 ? for 5 hours. The reaction mixture was and quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate/dichloromethane = 5/1/2) to give 830 mg of the titled compound as a yellow solid (Yield: 66%). [461] 1H NMR (CDCl3, 400 MHz) delta 8.20(m, 4H), 7.85(d, 1H), 7.30(d, 2H), 5.54(brs, 1H), 3.71(s, 3H), 2.57(m, 2H), 2.44(s, 3H), 0.94(t, 3H)

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

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 1865-29-8, name is Methyl 2-phenylacrylate, I believe this compound will play a more active role in future production and life. 1865-29-8

A solution of LiAlD4 (95 mg, 2.3 mmol) and AlCl3 (100 mg, 0.75 mmol) in THF was allowed to stir for 10 minutes before the addition of ester 16 (120 mg, 0.74 mmol) in THF. After 1.5 hours, the solution was quenched by addition of H2O, extracted with ether, and the ether extracts were dried (MgSO4) and concentrated in vacuo. The resulting oil was purified via flash column chromatography (15% EtOAc in hexane) to give the desired product 19 as a white solid (35 mg, 35%).

The chemical industry reduces the impact on the environment during synthesis 1865-29-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Richardson, Rebekah M.; Barney, Rocky J.; Wiemer, David F.; Tetrahedron Letters; vol. 53; 49; (2012); p. 6682 – 6684;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

25542-62-5, 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. 25542-62-5, name is Ethyl 6-bromohexanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedeure: In a 250-mL round-bottom flask, 4-hydroxybenzaldehyde (5g, 41 mmol, 1eq.) and K2CO3( 14g,101 mmol, 2.5eq) were dissolved in anhydrous DMF (25 mL). Ethyl 6-bromohexanoate (13.7g, 61 mmol, 1.5 eq.) was slowly added to the solution under nitrogen atmosphere and refluxed for 2-4 h. Reaction was monitored by TLC. The solution was filtered over Celite 535, diluted with ethyl acetate (150 mL), and washed with brine (100 mLx2). The organic phase was dried over MgSO4, filtered, and concentrated. The crude product, a colorless oil (10.66 g, 40 mmol, 99%), was used without further purification.

The synthetic route of Ethyl 6-bromohexanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mitachi, Katsuhiko; Salinas, Yandira G.; Connelly, Michele; Jensen, Nicholas; Ling, Taotao; Rivas, Fatima; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4536 – 4539;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 61644-18-6, name is Chloromethyl isobutyrate, I believe this compound will play a more active role in future production and life. 61644-18-6

A mixture of chloromethyl 2-methylpropanoate (1.5 eq), tert-butyl hydrogen fumarate (0.5 g, 1.0 eq), and Cs2CO3 (2.0 eq) in N-methylpyrrolidone (10 mL) was stirred between 50 to 70 C. overnight. The reaction was concentrated in vacuo to a residue, diluted with ethyl acetate, and washed with water, saturated bicarbonate solution and brine. The organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo to yield the crude product. The crude material was then purified by silica gel column chromatography using ethyl acetate and hexanes to yield compound (6a).

The chemical industry reduces the impact on the environment during synthesis 61644-18-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nguyen, Mark Quang; (47 pag.)US2016/229819; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, name is tert-Butyl methyl malonate, 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. 42726-73-8

Tert-butyl methyl malonate (2.64 g, 15.14 mmol) was dissolved in THF (50 mL). Sodium hydride (0.605 g, 15.14 mmol) was added portion-wise at 0 ¡ãC and the reaction mixture was allowed to stir for 15 mm at room temperature. 2-chloro-5-nitropyridine (2.012.61 mmol) dissolved in 10 mL of THF was then added to the mixture and the mixture was allowed to stir for 4 hours at room temperature before being quenched withsaturated aqueous ammonium chloride and extracted with EtOAc (3x). The combined organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The resulting residue was dissolved in 30 mL of 2:1 DCMITFA and stirred for 1.5 hours. The reaction mixture was then diluted with 1.5 M potassium phosphate solution and extracted with EtOAc (3x). The combined organic layer was washed with brine, driedwith sodium sulfate, filtered and concentrated. The resulting residue was dissolved in methylene chloride before being charged to an 80 g silica gel cartridge which was eluted with a 30 mm gradient from 0-100percent EtOAc in hexane. Fractions containing the desired product were concentrated to yield Intermediate I-109A (1.06 g, 5.40 mmol, 42.8 percent yield), as a yellow oil. LC-MS: Method H, MS (ESI) m/z: 197.0 (M+H). ?H NMR(400MHz, CDC13) 9.41 (d, J=2.6 Hz, 1H), 8.49 (dd, J8.6, 2.6 Hz, 1H), 7.56 (d, J8.6 Hz, 1H), 4.02 (s, 2H), 3.78 (s, 3H).

Statistics shows that 42726-73-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl methyl malonate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

701-83-7, These common heterocyclic compound, 701-83-7, name is 3-Fluorophenyl 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.

EXAMPLE 16 Preparation of 4′-Fluoro-2′-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C. for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid. The resultant mixture is stirred for several minutes, and the phases are separated. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (99.0 g) which is identified by 1H NMR spectral analysis.

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 701-83-7.

Reference:
Patent; BASF Aktiengesellschaft; US6355796; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 18927-05-4, name is Methyl 3-Methoxyphenylacetate, molecular formula is C10H12O3, 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. 18927-05-4

Methyl bromo(3-methoxyphenyl)acetate; A mixture of 15.7 g (87.1 mmol) of methyl (3-methoxyphenyl)acetate, 16.3 g (91.5 mmol) of Lambda/-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (150 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered and the solvent was removed in vacuo. Yield: 21.8 g (100%) of yellow oil 1H-NMR (DMSOd6): 3.72 (s, 3H), 3.76 (s, 3H), 5.90 (s, 1 H), 6.92-6.97 (m, 1 H), 7.08- 7.13 (m, 2H), 7.28-7.34 (m, 1 H). MS (API-ES,pos) m/z = 261 [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 18927-05-4, its application will become more common.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics