Author: Jessica.F

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 13031-39-5 as follows. HPLC of Formula: C8H7ClO2

3-chlorophenyl acetate (starting material 2) was mixed with aluminium chloride (3 eq). The mixture was heated at 200 C. for 1 hour. The reaction medium was cooled to room temperature then poured in ice. The aqueous phase was extracted with methylene chloride which was dried on magnesium sulfate then vacuum evaporated. Purification was by silica gel chromatography (elution: cyclohexane/ethyl acetate 95:5). 1 H NMR CDCl3 deltappm: 3.41 (s, 3 H), 6.81 (dd, J=8.82 Hz, J=1.47 Hz, 1H), 6.91 (d, J=1.47 Hz, 1H), 7.60 (d, 8.82 Hz, 1 H), 12.33 (s, 1H) Reference: Chen et al, J Chem Soc, 1958, 146-148.

According to the analysis of related databases, 13031-39-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENFIT; US2005/171149; (2005); A1;,
Ester – Wikipedia,
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19063-56-0, name is 7-Bromo-2H-chromen-2-one, 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: 7-Bromo-2H-chromen-2-one

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

The synthetic route of 19063-56-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
Ester – Wikipedia,
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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. 14659-60-0, name is Methyl 4-fluoro-2,6-dimethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H11FO2

4-Amino-2,6-dimethyl benzoic acid (200 mg, 1.1 mmol) and NOBF4 (196 mg, 1.7 mmol) were heated in 1,2-dichlorobenzene at 100 C for 30 min. The solution was cooled and diluted with MeOH and water. A few pellets (2-3) of KOH were added, and the solution was heated at reflux for 16 h. The solution was concentrated. The residue was partitioned between Et2O and 1 N NaOH. The aqueous layer was extracted with Et2O. The aqueous layer was cooled to 0 C and acidified with conc. HCl (pH = 1-2). The aqueous layer was extracted with CH2Cl2. The organic layers were dried (Na2SO4). Filtration and concentration gave 58 mg (31 %) of the acid as a tan solid.

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 14659-60-0.

Reference:
Patent; SCHERING CORPORATION; EP1175401; (2005); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 31273-66-2, name is Ethyl 2,3-dichlorobenzoate, 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 31273-66-2, Safety of Ethyl 2,3-dichlorobenzoate

General procedure: A mixture of substituted ethyl benzoate (12a-g) (0.1M) and hydrazine hydrate (0.3M) was heated under reflux for 30min. Ethanol (20mL) was added to the refluxing mixture as a solvent in order to homogenize the solution, the resulting mixture was further allowed for 6h. Excess of ethanol was distilled out and the content was allowed to cool. The crystals formed were filtered and washed thoroughly with water and dried.

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; Rakse, Monika; Karthikeyan, Chandrabose; Deora, Girdhar Singh; Moorthy; Rathore, Vandana; Rawat, Arun K.; Srivastava; Trivedi, Piyush; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 469 – 476;,
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Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, 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. COA of Formula: C9H8O4

General procedure: (i) [Ir(coe)2Cl]2 (0.9 mg, 0.1mol %) and aryl acetates 1 (1 mmol) were added to a flame-dried, nitrogen-purged septum-capped vial. The mixture was dissolved with THF (0.3 mL, 3.3 M), and diethylsilane (0.26 mL, 2 mmol) was added to the mixture. The septum on the vial was replaced by a screw cap with a Teflon liner under a N2 atmosphere [note: diethylsilane (bp 56 C and density 0.686 g/mL) is volatile]. The reaction mixture was stirred for 3-12 h at 60 C. Volatiles were removed in vacuo to afford silyl acetals, which were directly used for subsequent reactions without further purification. (ii) [Rh(nbd)Cl]2 (1.8 mg, 0.4 mol %), tris(4-methoxyphenyl)phosphine (8.4 mg, 2.4 mol %), norbornene (188 mg, 2 mmol), and THF (1 mL, 1M) were added to the crude silyl acetals (1 mmol). The septum on the vial was replaced by a screw cap with a Teflon liner, and the mixture was stirred at 120 C for 15 min. The reaction progress was monitored by GC/MS spectrometry. The resulting benzodioxasilines 3 were directly used for a subsequent reaction without further purification. For hindered substrates 3o-r, the resulting benzodioxasilines 3 were purified for the subsequent reactions; volatiles were removed in vacuo, and the resulting mixture was dissolved with pentane, filtered through a pad of Celite, and concentrated in vacuo. The crude product was purified by MPLC (hexanes/EtOAc=80:1, 5mL/min, retention time 5-15 min). (iii) The crude benzodioxasilines 3 (1 mmol, THF, 1M) were diluted with diethyl ether (3 mL, 0.33 M) and cooled to -78 C. MeLi (3 mmol, 1.6 M in Et2O) were added into the reaction mixture at -78 C and stirred for 1 min. (iv) Trifluoromethanesulfonyl anhydride (1.2 mmol, 0.2 mL) was added into the reaction mixture. The reaction mixture was warmed to rt and stirred for 30 min. The reaction mixture was cooled to 0 C and saturated aqueous ammonium chloride solution was added. The mixture was extracted with diethyl ether three times. The combined organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. Volatiles were removed in vacuo, and the crude mixture was purified by MPLC to afford arylsilyl triflates 5 (hexanes/EtOAc=40:1, 5mL/min, retention time 6-20 min).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.

Reference:
Article; Asgari, Parham; Dakarapu, Udaya Sree; Nguyen, Hiep H.; Jeon, Junha; Tetrahedron; vol. 73; 29; (2017); p. 4052 – 4061;,
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Related Products of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Under argon, 1.28 ml (9.15 mmol) of diisopropylamine were initally charged in 6 ml of dry THF, and the mixture was cooled to -40 C. 4.26 ml (9.15 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise, and the mixture was stirred for 30 min. The reaction solution was then cooled to -78 C., and a solution of 1.30 g (9.15 mmol) of tert-butyl cyclopropanecarboxylic acid in 2 ml of THF was added. After 4 h of stirring at -78 C., a solution of 2.00 g (8.69 mmol) of 1-(bromomethyl)-2-methyl-3-nitrobenzene in 2 ml of THF was added. Slowly, the reaction mixture was warmed to RT overnight. Ammonium chloride solution was then added carefully, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 0.78 g (29.3% of theory) of the title compound.1H-NMR (400 MHz, DMSO-d6): delta=7.61 (d, 1H), 7.54 (d, 1H), 7.39 (t, 1H), 2.96 (s, 2H), 2.26 (s, 3H), 1.26 (s, 9H), 1.20 (q, 2H), 0.79 (q, 2H).

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

Reference:
Patent; BAYER SCHERING PHARMA AKTIEGESELLSCHAFT; US2011/34450; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

To a solution of LDA in THF (40 mL of a 0.8 M solution; 33.2 mmol) at -78 C. was added tert-butyl cyclopropane carboxylate (3.78 g, 26.6 mmol) dropwise over 10 min. The solution was stirred at -78 C. for 2 h, after which 1-bromopropane (4.84 mL, 53.2 mmol) was added dropwise over 20 min at -78. The reaction was allowed to slowly warm to RT and stirred overnight at RT, then was quenched with sat’d aq. NH4Cl and extracted with EtOAc (2*). The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was distilled under reduced pressure (20 torr, BP=95 C.) to give the title compound (2.99 g, 61% yield) as an oil. 1H NMR (500 MHz, CDCl3) delta 1.48 (m, 4H), 1.45 (s, 9H), 1.12 (m, 2H), 0.92 (m, 3H), 0.61 (m, 2H).

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; BRISTOL-MYERS SQUIBB COMPANY; SHI, YAN; Cheng, Peter Tai Wah; Wang, Ying; Shi, Jun; Tao, Shiwei; Li, Jun; Kennedy, Lawrence J.; Kaltenbach, III, Robert F.; Zhang, Hao; Corte, James R.; US2019/185446; (2019); A1;,
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These common heterocyclic compound, 4911-54-0, name is Ethyl 4-methylpent-4-enoate, 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. name: Ethyl 4-methylpent-4-enoate

EXAMPLE 13 The reaction is carried out as described in Example 8 but using catalyst 4a (7.6 mg, 0.01%) in THF (5 ml) and KOMe (0.63 g, 9 mmol) in ethyl 4-methylpent-4-enoate 11 (12.9 g, 91 mmol) and THF (58 ml). Standard work-up gave a slightly yellow crude oil (5.6 g, 61%) which contained 4-methyl pent-4-en-1-ol 12 of 100% purity according to GC. The analytical data of 4-methylpent-4-en-1-ol 12 were identical with the ones obtained from commercial samples of this compound.

The synthetic route of Ethyl 4-methylpent-4-enoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Geisser, Roger Wilhelm; Goeke, Andreas; Schroeder, Fridtjof; US2015/152029; (2015); A1;,
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Related Products of 19063-56-0, The chemical industry reduces the impact on the environment during synthesis 19063-56-0, name is 7-Bromo-2H-chromen-2-one, I believe this compound will play a more active role in future production and life.

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

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, 7-Bromo-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 264276-14-4,Some common heterocyclic compound, 264276-14-4, name is Dimethyl 2,6-dichloroterephthalate, molecular formula is C10H8Cl2O4, 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 the stirred solution of dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate (2 g, 7.6 mmol, Step b) in tetrahydrofuran and water (1:1, 20 mL), sodium hydroxide (304 mg, 7.6 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under vacuum and the residue was neutralized using cold hydrochloric acid (1N). The precipitated solid was filtered under suction, washed with hexane and dried to afford 3,5-dichloro-4-(methoxycarbonyl)benzoic acid as an white solid (1.5 g, 85%). 1H NMR (400 MHz, DMSO-d6): delta 7.93 (s, 2H), 3.94 (s, 3H). MS: 247.6 (M-2), 249.6 (M).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2,6-dichloroterephthalate, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; Verma, Ashwani Kumar; Nagaswamy, Kumaragurubaran; Sharma, Lalima; Ghosh, Soma; Kale, Balkrishna Ramchandra; Mondal, Aniruddha; Srivastava, Punit Kumar; Dastidar, Sunanda Ghosh; Momin, Rijwan Jaffer; Wagh, Pradip Balu; Pansare, Sonali Nanasaheb; Markad, Pramod Raosaheb; Khairnar, Yogesh Balasaheb; Miyauchi, Rie; Murata, Takeshi; Ishizaki, Masayuki; Nagamochi, Masatoshi; Iimura, Shin; US2014/155398; (2014); A1;,
Ester – Wikipedia,
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