Month: August 2021

Reference of 88709-17-5, 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. 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of ethyl 2-ethoxy-4-methylbenzoate 117 (10.0 g, 48.1 mmol) in a mixture of pyridine (25 mL) and water (75 mL) was added KMn04 (22.8g, 144.2 mmol). The resulting mixture was heated at 50 C for 48 hours, then cooled and allowed to stir at room (0540) temperature for 24 hours. The mixture was filtered and the filter cake washed with hot water. The combined aqueous filtrates were washed with EtOAc (75 mL x 3) and acidified with 2M aqueous HCI solution. The mixture was extracted with CH2CI2 (150 mL x 3). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated to give the desired compound as a white solid (5.0 g, 44%): LCMS: RT 0.25 min; m/z 239.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-ethoxy-4-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul Anthony; (88 pag.)WO2017/153519; (2017); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 56741-34-5, name is Methyl 5-amino-2-fluorobenzoate, 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 56741-34-5, Recommanded Product: Methyl 5-amino-2-fluorobenzoate

General procedure: To a solution of 11a (500 mg, 1.85 mmol) in acetone (10 mL) was added 12 (380 mg, 1.85 mmol) and pyridine (0.45 mL, 5.54 mmol).The mixture was stirred at 55 C for 1 h. The mixture was concentrated,diluted with ethyl acetate and washed with 1M HCl and brine twice.Then, the ethyl acetate layer was dried over anhydrous sodium sulfate andconcentrated to give the crude product. The crude product was purified bysilica column eluting with petroleum ether/ethyl acetate (5/1-2/1) to givethe desired product (0.33 g, yield 44.3%) as grey solid

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:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
Ester – Wikipedia,
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Related Products of 148547-19-7, 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. 148547-19-7 name is Methyl 4-bromo-3-methylbenzoate, 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.

Preparation 17; 3-(4-lodomethyl-2-methyl-phenyl)-propionic acid methyl ester; Step A; 3- (4-Hydroxvmethyl-2-methyl-phenyl)-acrylic acid methyl ester; A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24.88 mmol), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 X 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methylacrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o- tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 deg C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 mL, 1M). The product is extracted with dichloromethane (2 X 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1: 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M++1 207. The structure is confirmed by 1H NMR spectroscopy.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/66136; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 89-91-8, 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 89-91-8 as follows.

The synthesis of {5-Bromo-l-[3-(methylsulfonyl)propyl]-lH-benzimidazol-2-yl}- methanol (fragment A2) was done as shown in scheme 6. refluxed overnightfragment A2Scheme 6 Compound 1 (7.6 g, 35 mmol), 3 -(methyl sulfonyl)propan-l -amine hydrochloride (6 g, 35 mmol) and diisopropylethylamine (DIEA) (13.5 g, 105 mmol) were dissolved in ethanol (70 mL) and refluxed for 14 h. The mixture was cooled to 20C. The precipitate was filtered and washed with ethanol. 11 g (94%) of compound 2 was obtained as an orange powder. Compound 2 (10 g, 29.7 mmol) in methanol (200 mL), EtOAc (200 mL) and THF (200 mL) was hydrogenated with Raney Ni (10 g) as a catalyst at 20C (1 atm) for 3h. After uptake of H2 (3 eq), the catalyst was filtered off and the filtrate was evaporated. 10 g (90%) of compound 3 was obtained as a black solid.Compound 3 (10 g, 29.7 mmol) and methyl dimethoxyacetate (9.2 g, 68.31 mmol) in 24 wt% KOEt in ethanol (13.5 g, 38.5 mmol) were stirred and refluxed overnight. The mixture was evaporated under vacuum. Water (200 mL) was added. Acetic acid was added to neutralize the mixture. The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated NaHC03, brine and dried over Na2S04. The solvent was removed under vacuum to yield 12.3 g (90%) of compound 4 as dark oil. Compound 4 (12.3 g, 29.3 mmol) in THF (100 mL) was stirred for 0.5 h at 20C to dissolve. Cone. HCI (21 mL) and H20 (42 mL) were added.The mixture was refluxed for 6 h and then cooled to -10C. CH3OH (50 mL) were added, followed by careful addition of NaBH4 (24 g, 629 mmol). The mixture was stirred for 0.5 h at 10C and concentrated under vacuum. Water (200 mL) was added.The mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine and dried over Na2S04. The solvent was removed under vacuum. The resulting solid was washed with ethyl acetate (2×5 mL) and dried under vacuum. 6.8 g (60%) of fragment A2 was obtained as an off-white solid, m/z = 347 & 349 (M+H)+Br pattern. 1H NMR (400 MHz, DMS0 ) delta ppm 2.20 (dq, J=7.8, 7.5 Hz, 2 H), 2.98 (s, 3 H), 3.16 – 3.24 (m, 2 H), 4.42 (t, J=7.4 Hz, 2 H), 4.73 (d, J=6.0 Hz, 2 H), 5.73 (t, J=5.8 Hz, 1 H), 7.42 (dd, J=8.7, 1.9 Hz, 1 H), 7.63 (d, J=8.5 Hz, 1 H), 7.79 – 7.83 (m, 1 H)

According to the analysis of related databases, 89-91-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; COOYMANS, Ludwig Paul; DEMIN, Samuel Dominique; HU, Lili; JONCKERS, Tim Hugo Maria; RABOISSON, Pierre Jean-Marie Bernard; TAHRI, Abdellah; VENDEVILLE, Sandrine Marie Helene; WO2012/80446; (2012); A1;,
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. Application In Synthesis of Methyl 2-(3-bromophenyl)acetate

Sodium hydride (60% in oil) (10.4 g, 436 mmol) was added to tetrahydrofuran (400 ml) under argon and heated with stirring to 50 C. Methyl 2-(3-bromophenyl)acetate (20 g, 87.3 mmol) was added drop wise over 30 minutes and heating continued for 90 minutes. The temperature was lowered to below 40 C. and methyl iodide (13 ml, 209 mmol) was added over 10 minutes. The resulting suspension was stirred at room temperature overnight. Water (300 ml) was carefully added and reaction mixture concentrated. Residue was partitioned between diethyl ether (400 ml) and water. The aqueous layer was extracted with diethyl ether (400 ml), and the combined ethereal extracts were dried over sodium sulfate and concentrated. Crude oil was purified by column chromatography, eluding with a gradient from 0% to 20% ethyl acetate in heptane to give methyl 2-(3-bromophenyl)-2-methylpropanoate (14.96 g, 58 mmol, 67%). 1H NMR (400 MHz, CDCl3): delta ppm 7.47 (t, 1H), 7.37 (dt, 1H), 7.24 (dt, 1H), 7.18 (t, 1H), 3.65 (s, 3H), 1.55 (s, 6H)

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; pfizer Inc; US2010/197591; (2010); 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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

General procedure: A mixture of 8a-8j (10 mmol), 15a-15d (11 mmol) and K2CO3 (4.15 g, 30 mmol) in DMF (60 mL) was stirred at room temperature (for 15a-15b) or slightly elevated temperatures (35 C for 15d and 45 C for 15c) until the reaction completed as indicated by TLC analysis (typically within 12h). On cooling (if necessary), the reaction mixture was poured into ice-water (200 mL) and the resulting mixture was extracted with CH2Cl2 (100 mL 3). The combined extracts were washed with 5% brine (100 mL 5), dried (Na2SO4) and evaporated on a rotary evaporator to afford the crude product as a residue, which was purified by column chromatography followed by trituration with EtOAc/n-hexane (if the product was solid) to yield the pure product 9a-9q.

According to the analysis of related databases, 35120-18-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Wei; Liu, Yuqiang; Xie, Yafei; Shang, Qian; Zhou, Zhixing; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Medicinal Chemistry; vol. 13; 3; (2017); p. 260 – 281;,
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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. 42122-44-1, name is Methyl 3-(4-fluorophenyl)propiolate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C10H7FO2

The product thus obtained was dissolved in DMF (2,4 mL) and added slowly dropwise over 20 min to a cooled mixture (00C, ice bath) containing potassium carbonate (0.070 g, 0.50 mmol), methyl 3-(4-fluorophenyl)propiolate (0.030 g, 0.19 mmol) and DMF (2.0 mL). The mixture was kept in the cooling bath with stirring and allowed to proceed for 15 h at ambient temperature. The mixture was filtered and concentrated. Purification on silica gel (0-100% ethyl acetate/hexanes, 60 min gradient) afforded methyl 2-(4-fluorophenyl)-6-(N-(2- hydroxyethyl)methylsulfonamido)-5-(3-(2-phenylpropan-2-ylcarbamoyl)phenyl) pyrazolo[lj5-a]pyridme-3-carboxylate as a yellow residue. IH NMR (500 MHz, CHLOROFORM-D) delta ppm 8.72 (s, 1 H), 8.24 (s, 1 H), 8.16 (s, 1 H), 7.97 – 8.00 (m, 1 H), 7.89 (t, J-7.93 Hz, 1 H), 7,77 – 7.84 (m, 2 H), 7.50 – 7.59 (m, 2 H)5 7.40 – 7.49 (m, 3 H), 7.23 – 7.33 (m, 3 H)9 7.12 – 7.19 (m, 3 H), 3.83 (s, 3 H), 3.62 – 3.71 (m, 1 H), 3.39 – 3.46 (m, 1 H), 3.30 – 3.39 (m, 1 H), 3.18 – 3.23 (m, 3 H), 2.63 – 2.72 (m, 1 H), 1.78 (t, J=I 2.21 Hz, 6 H). LCMS: retention time: 2.403 min. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Waters- Sunfre, 5u, C 18, 4.6 x 50 mm column using a SPD-10AV UV- Vis detector at a detector wave length of 220 nM. The elution conditions employed a flow rate of 4 mL/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% CH3CN / 90% H2O / 10 mM TFA and solvent B was 10% H2O / 90% CH3CN / 10 mM TFA. MS data was determined using a Micromass Platform for LC in electrospray mode, m/z 645 (MH+).

The synthetic route of 42122-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PRACITTO, Richard; KADOW, John F.; BENDER, John A.; BENO, Brett R.; GRANT-YOUNG, Katharine A.; HAN, Ying; HEWAWASAM, Piyasena; NICKEL, Andrew; PARCELLA, Kyle E.; YEUNG, Kap-Sun; CHUPAK, Louis S.; WO2010/30538; (2010); A2;,
Ester – Wikipedia,
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Synthetic Route of 1459-93-4,Some common heterocyclic compound, 1459-93-4, name is Dimethyl isophthalate, molecular formula is C10H10O4, 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.

Magnesium (6.53 g, 25.75 mmol) was suspended in anhydrous THF (50 mL). The solution was cooled at -5 C in a ice-salt bath and a solution of (E)-1-(3-bromobut-1-enyl)benzene 3 (5.43g, 25.75 mmol) in THF (30 mL) was added dropwise over 1h at such a rate that the internal reaction temperature did not exceed 0C. Upon completion of the addition, the reaction mixture was stirred for 1h from 0 to -10 C. The solution was cooled to – 80 C in a liquid nitrogen-acetone freezing mixture. A solution of dimethylisophthalate (5 g, 25.75 mmol) in THF (40 mL) was added dropwise during 1h with vigorous stirring. Then the mixture was stirred at room temperature overnight. A 10% aqueous solution of H2SO4 (100mL) was added to the cooled reactionmixture. Two phases separated and the aqueous layer was extracted with ether (2×50 mL). The combined ethereal extracts were successively washed with a saturated aqueousNaHCO3 solution, water and finally dried over anhydrous magnesium sulfate. After removal of solvent, the resulting residue was purified on a silicagel column eluted with hexane/ethyl acetate 20:1 to give the corresponding aryl ketone(77%). []D20 = – 5.2 (c 0.1 AcOEt) with spectral data identical to those of product from procedure 1.

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

Reference:
Article; Mezrai; Drici; Lesur; Kajima Mulengi; Wadouachi; Pilard; Letters in Organic Chemistry; vol. 11; 4; (2014); p. 259 – 267;,
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Ester – an overview | ScienceDirect Topics

Application of 87-24-1, 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. 87-24-1, name is Ethyl 2-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(a) A mixture of 100 g. of ethyl o-toluate, 100 g. of N-bromosuccinimide, and 0.3 g. of benzoyl peroxide in 1 liter of carbon tetrachloride is heated under reflux for 3 hours with stirring and filtered. The filtrate is washed with 3% aqueous sodium hydroxide and then with water, dried over magnesium sulfate, and concentrated under reduced pressure to provide ethyl alpha-bromo-o-toluate as an oil.

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

Reference:
Patent; American Hoechst Corporation; US4585788; (1986); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 758684-29-6,Some common heterocyclic compound, 758684-29-6, name is Methyl 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate, molecular formula is C10H11NO3, 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.

Triethylamine (0.065 mL, 0.466 mmol) and benzoyl chloride (0.022 mL, 0.186 mmol) were added to a solution of methyl 3,4-dihydro-2H-benzo[b][l,4]oxazine-6-carboxylate (30 mg, 0.155 mmol) in 1,2-dichloroethane (2mL), and the reaction stirred at ambient temperature overnight. The reaction was diluted with dichloromethane and washed with brine. The organic layer was passed through an Isolute phase separator, and then concentrated to afford a quantitative yield of methyl 4-benzoyl-3,4-dihydro-2H-benzo[b][l,4]oxazine-6- carboxylate which was used directly in the next step without further purification. MS: (ES, m/z): 298 [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 3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylate, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; NG, Pui, Yee; THOMASON, Jennifer, R.; ZABLOCKI, Mary-Margaret; HAN, Bingsong; BARCZAK, Nicholas; LIU, Cuixian; RUDNITSKAYA, Aleksandra; LANCIA JR., David, R.; BAIR, Kenneth, W.; (315 pag.)WO2017/40963; (2017); A1;,
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Ester – an overview | ScienceDirect Topics