Category: esters-buliding-blocks

Related Products of 6836-21-1, 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. 6836-21-1 name is Ethyl 2-(7-methoxynaphthalen-1-yl)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.

150 ml of ethanol is loaded into a three-necked reaction flask, magnetically stirred and equipped with a temperature probe, and cooled to 5C. When the temperature of 5C has been reached, 11.3 g of powdered calcium chloride(0.102 mol) is added, followed by 8.2 g of sodium borohydride (0.217 moles). After a few minute stirring at 5C, 10 g of 2-(7-methoxynaphthalen-1-yl)acetic acid ethyl ester 4 (41 mmols), dissolved in 100 ml of anhydrous THF, is added, the temperature being maintained under 10C. At the end of the addition the temperature is increased to room temperature and maintained at that temperature for about 2 hours. 5 ml of water is added slowly at the end of the reaction. 40 ml oftoluene and 20 ml of 30% HCl are then added. The phases are separated by re-extracting the aqueous phase with 20ml of toluene. The combined organic phases are washed with 40 ml of water, and then concentrated under vacuum to dryness to obtain 8.0 g of 2-(7-methoxynaphthalen-1-yl)ethanol 12. Yield 97%. The intermediate obtained was identifiedby NMR analysis: 1H NMR (400 MHz, DMSO-d6) delta 7.83 (d, 2H), 7.70 (m, 1H), 7.36 (m, 2H), 7.27 (m, 1H), 7.18 (m, 1H),3.92 (s, 3H), 3.75 (t, 2H), 3.29 (s, 1H), 3.19 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-(7-methoxynaphthalen-1-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; Procos S.p.A.; Barozza, Alessandro; Veronese, Martino; Roletto, Jacopo; Paissoni, Paolo; EP2703383; (2014); 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. 251085-87-7, name is Methyl 5-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Methyl 5-bromo-2-chlorobenzoate

5-Bromo-2-chlorobenzaldehyde (74c). A solution of pyrrolidine (4.00 g, 56.0 mmol) in MTBE (12 mL) was added dropwise over 20 min to a solution of Red-Al (3.4 M solution in toluene, 16 ml, 54.4 mmol) in MTBE (33 mL) maintained at -20 C. The mixture was stirred for 1 h at 25 C. A solution of potassium tert-butoxide (0.60 g, 5.36 mmol) in THF (3 mL) was added. The resulting solution was added dropwise to a solution of 2-chloro-5-bromobenzoic acid methyl ester (72, 6.80 g, 27.3 mmol) in MTBE (15 mL) at 10 C. After 15 min the mixture was quenched with 2 N HCl (300 mL). Repeated recystallizations (hexanes) of the recovered material gave a crude solid (3.22 g, 54%, mp 43-46 C), which was used without further purification in the next step.; The synthesis of benzaldehyde chlorooxime synthons 52 is depicted in Scheme 4, below. Of the eight aldehydes 44e-f and 74a-f, only 44e and 74d were commercially available. The preparation of aldehyde 44f began with the known three-step transformation of 4-methyl-3-nitrobenzonitrile 63 to methoxy compound 64. See Reiner, J. E., et al., Bioorg. Med. Chem. Lett., 12, 1203-1208 (2002). alpha-Bromination of 64 using one equivalent of N-bromosuccinimide gave little selectivity between the mono- and dibromo adducts, but the analogous reaction using 2.5 equivalents gave dibromide 65 almost exclusively. Silver nitrate oxidation of dibromide 65 gave aldehyde 44f. See Hill. R. A., et al., J. Chem. Soc., Perkin Trans., 1, 2209-2215 (1987). The reaction of the o-nitrotoluene 63 with N,N-dimethylformamide dimethyl acetal in DMF gave the enamine 66, which underwent oxidative cleavage using sodium periodate in THF, see Riesgo, E. C., et al., J. Org. Chem., 61, 3017-3022 (1996), to give aldehyde 74a via a more facile preparation than previously reported. See Dann, O., et al., Liebigs Ann. Chem., 3, 409-425 (1984). Aldehyde 74b also has been prepared previously. See Schultz, E. M., et al., J. Med. Chem., 19(6), 783-787 (1976). A more expedient preparation of 74b began with chlorotoluene 67 undergoing alpha-bromination to 68, see Gilbert, A. M., et al., J. Med. Chem., 43, 1203-1214 (2000), by a modification of the original procedure. See Liu, P., et al., Synthesis, 14, 2078-2080 (2001). The reaction of 68 with 2-nitropropane and sodium ethoxide in ethanol gave 74b. See Mallory, F. M., et al., Tetrahedron, 57, 3715-3724 (2001). Commercially available aldehyde 69 and aldehyde 71, see Hino, K., et al., Chem. Pharm. Bull., 36(6), 3462-3467 (1988), which had been prepared via a Sandmeyer reaction from commercially available 70, were converted to methyl esters 72 and 73, respectively. The esters were converted to aldehydes 74c and 74e, respectively, using Red-Al(sodium bis(2-methoxyethoxy)aluminium hydride) (Aldrich Chemical Co., Inc., Milwaukee, Wisconsin, United States of America), pyrrolidine, and potassium tert-butoxide in methyl tert-butyl ether. See Abe, T., et al., Tetrahedron, 57, 2701-2710 (2001). Cyanoaldehyde 74f was prepared by debromocyanation of 44d. See Laali, K. K., et al., J. Org. Chem., 58, 1385-1392 (1993). Aldehydes 44e-44f and 74a-74f were converted to oxime derivatives 75a-h (of which 75a,e were known previously), see Quan, M. L., et al., J. Med. Chem., 42(15), 2752-2759 (1999), using hydroxylamine hydrochloride in either water/ethanol or pyridine/ethanol. The oximes were treated with N-chlorosuccinimide in DMF to give chlorooximes 52a-h, following the procedure reported for 52e. See Liu. K.-C., et al., J. Org. Chem., 45, 3916-3918 (1980). The chlorooximes 52 were reacted with acetylenes 51 without further purification.; Reagents and conditions: (a) H2, 10% Pd/C, EtOH; (b) NaNO2, aq. H2SO4; (c) CH3l, NaH, DMF; (d) NBS, benzoyl peroxide, CCl4; (e) AgNO3, aq. EtOH; (f) DMFDMA, DMF; (g) NalO4; aq. THF; (h) diethyl phosphite, (i-Pr)2NEt, THF; (j) 2-nitropropane, NaOEt, EtOH; (k) NaNO2, aq. HCl, then CuCN, KCN; (I) MeOH, H2SO4; (m) DCC, DMAP, MeOH, CH2Cl2; (n) Red-Al, t-BuOK, pyrrolidine, MTBE; (o) NH2OH HCl, H2O/EtOH or Py/EtOH (p) NCS, DMF.

The synthetic route of 251085-87-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; EP1719767; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 63243-76-5, name is Ethyl 2-amino-5-bromobenzoate, 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. HPLC of Formula: C9H10BrNO2

[00384] The mixture of 2-amino-5-bromo-benzoic acid ethyl ester (3.0 g, 13.16 mmol) and (0979) cyclopropanecarbonitrile (2.6 g, 39.47 mmol) in 6 M HCl/dioxane (60 mL) was stirred at reflux overnight. The solid was filtered, dried in vacuum to give 6-bromo-2-cyclopropyl-quinazolin-4-ol (3.3 g, yield: 95%) as crude product. MS: m/z 249.1 (M+H+).

The synthetic route of Ethyl 2-amino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEDRICK Michael P.; HERSHBERGER Paul M.; MALONEY Patrick R.; PEDDIBHOTLA Satyamaheshwar; PINKERTON Anthony B.; WO2015/200534; A2; (2015);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 2216-45-7, name is 4-Methylbenzyl acetate, A new synthetic method of this compound is introduced below., SDS of cas: 2216-45-7

General procedure: A mixture of benzonitrile (5 mmol), benzyl acetate (6 mmol),and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomedflask. Then, the reaction mixture was heated at 80 C for 5 h.After completion of the reaction monitored by thin layer chromatography(TLC), water (10 mL) was added, and the reactionmixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were collected, combined, washed with water(3 × 20 mL), dried with anhydrous Na2SO4, and concentratedunder vacuum. The pure product was obtained by directlypassing through a silica gel (200-300 mesh) column to give awhite powder a (0.91 g, 87% yield)..

The synthetic route of 2216-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 35005-25-5, The chemical industry reduces the impact on the environment during synthesis 35005-25-5, name is Isopropyl 3-aminobenzoate, I believe this compound will play a more active role in future production and life.

3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoic acid (1.0 equiv) and isopropyl 3-aminobenzoate (1.2 equiv) were mixed in DMF, and the resulting mixture was added to HATU (1.5 equiv) and DIPEA (1.5 equiv). The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure, and the obtained residue was diluted with EtOAc and washed with water and brine. An organic layer was collected and dehydrated with anhydrous MgSO4, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography, thereby obtaining isopropyl 3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)benzoate (transparent liquid, 0.06 g, 26.5% yield). (0364) 1H-NMR (500 MHz, CDCl3) 7.99 (brs, 2H), 7.93 (d, J=7.0 Hz, 1H), 7.79 (d, J=7.0 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.32 (d, J=9.0 Hz, 2H), 6.89 (d, J=8.0 Hz, 2H), 5.25 (m, 1H), 4.35 (t, J=6.0 Hz, 2H), 2.87 (t, J=6.0 Hz, 2H), 1.72 (s, 2H), 1.38 (d, J=6.5 Hz, 6H), 1.36 (s, 6H), 0.72 (s, 9H); 13C-NMR (125 MHz, CDCl3) delta 169.2, 165.7, 155.6, 143.4, 137.9, 131.6, 129.1, 127.3, 125.3, 124.3, 120.6, 113.8, 68.6, 64.1, 56.9, 38.0, 37.8, 32.3, 31.8, 31.7, 21.9.

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, Isopropyl 3-aminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DONGGUK UNIVERSITY GYEONGJU CAMPUS INDUSTRY-ACADEMY COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; Lee, Kyeong; Won, Mi Sun; Ban, Hyun Seung; Kim, Minkyoung; Kim, Bo Kyung; (40 pag.)US2020/31764; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 179688-27-8,Some common heterocyclic compound, 179688-27-8, name is Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate, molecular formula is C15H23NO6, 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 62 N’-[2-Carbethoxy-4,5-bis(2-methoxyethoxy)phenyl]-N,N-dimethylformamidine To a stirred solution of 15.7 g (50 mmol) of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate (WO-96130347) in 50 ml of DMF at 0 C. was added phosphorous oxychloride (5.6 ml, 60 mmol) during 15 m. The resulting solution was heated at 55 C. for 45 m, cooled, diluted with methylene chloride, and treated at 0 C. with 200 ml of N/1 sodium hydroxide during 2 m. The organic layer was separated and washed at 0 C. with water. The solution was dried and evaporated with added toluene present to give 18.4 g of amber oil; NMR (CDCl3) delta6 3.02 (s, Me2N).

The synthetic route of 179688-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6288082; (2001); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

1732-08-7, name is Dimethyl pimelate, 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. Quality Control of Dimethyl pimelate

To a 500 ml four-necked flask equipped with a stirring, a thermometer, a reflux condenser, and a constant pressure dropping funnel, 100 g of chloroform, 18.8 g (0.1 mol) of dimethyl 1,7-pimelate, and 0.6 g of 40 wt% were added. Hydrobromic acid, 72.0 g of bromine and 50 g of chloroform were added dropwise at 30-35 C. After the completion of the dropwise addition, the reaction was stirred at 30-35 C for 7 hours, cooled to 20-25 C, and purged with nitrogen for 2 hours. 17 wt% ammonia water, stirring reaction at 60-65 C for 6 hours, then, cooling to 20-25 C, adding 20 g of 30 wt% hydrogen peroxide, stirring at 30-35 C for 4 hours, adding 45 g of 20 wt% aqueous sodium hydroxide solution, The reaction was stirred at 30-35 C for 4 hours, layered, and the organic phase was washed twice with water. Each time 20 g of water, the aqueous phase is combined, the pH of the aqueous phase is adjusted to 2.5-2.0 with hydrochloric acid, filtered, and dried to obtain 15.1 g of a white solid 2,6-pyridinedicarboxylic acid, the liquid phase purity is 99.5%, and the product yield is 90.4%. .

The synthetic route of 1732-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Ju Lizhu; Zhang Mingfeng; Lv Qiangsan; Qi Yuxin; (7 pag.)CN110229096; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 167760-75-0,Some common heterocyclic compound, 167760-75-0, name is Methyl 4-amino-3-(trifluoromethyl)benzoate, molecular formula is C9H8F3NO2, 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.

Sodium nitrite (1.21 g, 0.017 mmol) was added to tetrafluoro boric acid (20 mL) in lot wise manner at -10C. The solution was stirred for 1 h at same tempreture then added methyl 4- amino-3-(trifluoromethyl)benzoate (3.5 g, 0.0 15 mmol) and continued stirring for h at sametempreture followed by addition of solution of KI (3.18 g, 0.0 19 mmol) in acetone : water (40 mL:60 mL).The reaction mass was stirred at rt for 1 h. The reaction mass was diluted with water and filtered to afford 4.8 g of title compound. ?H NMR (300 MHz, CDC13): 8.28 (s, 1H), 8.15-8.12 (d, J= 8.1Hz, 1H), 7.84-7.81 (d, J= 8.1Hz, 1H), 3.95(s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-amino-3-(trifluoromethyl)benzoate, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 210530-71-5, 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 210530-71-5 as follows.

To a stirred mixture of methyl 2- (3, 4-difluorophenyl) acetate (4.5 g, crude) in CCl4 (50 mL) was added NBS (6.0 g, 33.7 mmol) and HBr/HOAc (1.0 mL) . After the addition, the reaction mixture was stirred for 3 hours at 85. The solid of the reaction was filter out, the filtrate was concentrated, and this residue was dissolved by H2O (50 mL) , extracted with EtOAc (50 mL x 3) , The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give methyl 2-bromo-2- (3, 4-difluorophenyl) acetate (4.0 g, crud) as a yellow oil. MS: M/e 266 (M+1)+

According to the analysis of related databases, 210530-71-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; ZHANG, Guoliang; SUN, Hanzi; ZHOU, Changyou; (253 pag.)WO2020/20097; (2020); 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 2967-93-3 as follows. Formula: C9H9FO2

Step 2; Preparation of 2-Fluoro-5-formyl-benzoic acid methyl ester; Add Af-bromosuccinimide (2.46 g, 13.86 mmol) and benzoyl peroxide (0.152 g, 0.630mmol) to a solution of 2-fluoro-5-methyl-benzoic acid methyl ester (1.06 g, 6.30 mmol)in carbon tetrachloride (50 mL). Heat the mixture at reflux for 4 h. Cool the mixture toroom temperature and wash with saturated aqueous sodium bicarbonate solution (10 mL)and brine (10 mL). Dry the organic layer over anhydrous sodium sulfate, filter, andconcentrate under reduced pressure. Dissolve the resulting residue in dimethylsulfoxide(30 mL) and heat at reflux for 16 h. Cool the mixture to room temperature and dilutewith water (100 mL) and ethyl acetate (100 mL). Extract the aqueous layer with ethylacetate (3 x 100 mL). Wash the combined organic layers with water (3 x 100 mL),followed by brine (100 mL). Dry the organic layer over anhydrous sodium sulfate, filterand concentrate. Purify the residue by chromatography over silica gel, eluting withhexanes/ethyl acetate (80:20), to provide the title compound as a tan solid (0.228 g, 20%).

According to the analysis of related databases, 2967-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/2342; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics