Category: esters-buliding-blocks

Electric Literature of 106896-49-5, A common heterocyclic compound, 106896-49-5, name is Methyl 4-amino-3-bromobenzoate, molecular formula is C8H8BrNO2, 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 1c Preparation of 3-Bromo-4-cyano-benzoic acid methyl ester A solution of 4-Amino-3-bromo-benzoic acid methyl ester (1.00 g, 4.35 mmol) in dichloromethane (20 mL) is cooled to -10 C. and treated dropwise with 90% tert-butyl nitrite (0.58 g, 0.67 mL, 5.08 mmol) followed by boron trifluoride diethyl etherate (0.94 g, 0.81 mL, 6.62 mmol). The suspension is allowed to warm to room temperature and stirred for 4 h. Diethyl ether (20 mL) is added, and the off-white solid is collected by filtration, washed with diethyl ether and dried briefly under high vacuum. The solid is then suspended in toluene (15 mL) and cooled to 0 C. A solution of copper (I) cyanide (0.52 g, 5.8 mmol) and sodium cyanide (0.71 g, 14.5 mmol) in water (10 mL) is added dropwise over 10 min. The mixture is stirred at 0 C. for 30 min, allowed to warm to room temperature, and then heated to 60 C. After 1 h, the solids are completely dissolved. The mixture is allowed to cool to room temperature, and ethyl acetate (20 mL) and water (20 mL) are added. The aqueous layer is separated and extracted with ethyl acetate (2*20 mL). The organic layers are combined, washed with water (2*10 mL) and brine, dried over Na2SO4, filtered and concentrated at reduced pressure. The solid residue obtained is recrystallized from hexanes/ethyl acetate to afford 3-Bromo-4-cyano-benzoic acid methyl ester (0.42 g, 39%) as a tan solid. The recrystallization mother liquor is concentrated and chromatographed (Biotage, 95:5 to 85:15 hexanes/ethyl acetate) to afford an additional portion of 3-Bromo-4-cyano-benzoic acid methyl ester (0.34 g, total yield: 0.76 g, 73%).

The synthetic route of 106896-49-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; US2008/119457; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 55954-23-9, 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. 55954-23-9, name is Methyl 2,4-dichlorophenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0198] To the mixture of methyl 2-(2,4-dichlorophenyl)acetate (0.5 g, 2.29 mmol) in THF (10 mL) was added NaH(0.12 g, 2.98 mmol) at oo C. portionwise, then the mixturewas stirred at 25 C. for 0.5 hr, then to the mixture was addedMel (0.42 g, 2.98 mmol) dropwise, the mixture was stirred at25 C. for 2 hrs. After the starting material was consumedcompletely detected by TLC, the mixture was quenched byH20 (lOmL), extracted withEtOAc (10mL*3). The organicswere dried over Na2S04 and concentrated in vacuum to getthe title compound (0.3 g, yield: 50.8%) as yellow oil.

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 2,4-dichlorophenylacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; Hodous, Brian L.; (150 pag.)US2016/31892; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 3618-04-0, 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. 3618-04-0 name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

tert-Butyldimethylsilyl chloride (26.3 g, 174 mmol) was added to a solution of ethyl 4- hydroxycyclohexanecarboxylate (25.0 g, 145 mmol, mixture of cis-/trans-isomers, Gas No 17159-80-7) and imidazole (24.7 g, 363 mmol) in DMF (36 ml) and the mixture was stirred overnight at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtered through a silicone filter and concentrated under reduced pressure to yield ethyl 4-{[tert- butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104% yield) which was used in the next step without further purification.1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m,0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; WAGNER, Sarah; SUeLZLE, Detlev; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; (232 pag.)WO2018/78009; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

27492-84-8, name is Methyl 4-amino-2-methoxybenzoate, 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. Computed Properties of C9H11NO3

To a stirred solution of methyl 4-amino-2-methoxybenzoate (10 g, 55 mmol) in dichloromethane (100 mL) was added triethylamine (15.4 mL, 110 mmol) at 0 C and the mixture was stirred for 15 mm. To this mixture, acetyl chloride (5.68 g, 71 mmol) was added drop wise and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of water (75 mL). The organiclayer was separated, washed with brine solution (100 mL), dried over sodium sulfate and concentrated under reduced pressure to afford methyl 4-acetamido-2- methoxybenzoate (13.0 g, 58.2 mmol, quantitative yield) as a yellow solid: LCMS (ESI) m/e 224.2 [(M+H), calcd for C11H14N04, 224.1]; LC/MS retention time (method B): tR = 1.21 mm.

The synthetic route of 27492-84-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; BRONSON, Joanne J.; DZIERBA, Carolyn Diane; MACOR, John E.; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; WO2015/6100; (2015); A1;,
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Reference of 91367-05-4, A common heterocyclic compound, 91367-05-4, name is Methyl 4-chloro-3-methylbenzoate, molecular formula is C9H9ClO2, 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 methyl 4-chloro-3-methylbenzoate (4.0 g, 21.67 mmol) in CCl4 (150 mL) was added NBS (4.6 g, 25.99 mmol) and the suspension was heated at 80 C for 5 min and AIBN (1.78 g, 10.84 mmol) was added. The suspension was continued to stir at 80 C for 16 h. The mixture was cooled to RT and filtered. The filtrate was concentrated to give the crude product, which was purified by silica gel chromatography eluting with EA/petroleum ether from 0% to 3% to give methyl 3-(bromomethyl)-4-chlorobenzoate (4.92 g, 86.6%) as a white oil.

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; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
Ester – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6290-49-9, name is Methyl 2-methoxyacetate, 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 6290-49-9, SDS of cas: 6290-49-9

TiCl4 (664 mg, 3.50 mmol) and Et3N (405 mg, 4.00 mmol) were successively added dropwise to a stirred solution of methyl methoxyacetate (104 mg, 1.00 mmol), hexanoyl chloride (135 mg, 1.00 mmol), and 1,2-dimethylimidazole (115 mg, 1.20 mmol) in CH2Cl2 (3 mL) at -50 – -45 C under an Ar atmosphere, and the mixture was stirred at the same temperature for 1 h. Water was added to the mixture, which was extracted twice with Et2O. The combined organic phase was washed with sat. aq. NaHCO3 solution, brine, dried (Na2SO4), and concentrated. The obtained crude product was purified by SiO2-column chromatography (hexane/AcOEt = 80:1 – 50:1) to give the desired product (162 mg, 80%). Colorless oil; 1H NMR (300 MHz) delta 0.88 (3H, t, J = 7.2 Hz), 1.20-1.41 (4H, m), 1.58 (2H, quin, J = 7.2 Hz), 2.60 (1H, dt, J = 7.2 Hz, Jgem = 3.4 Hz), 2.61 (1H, dt, J = 7.2 Hz, Jgem = 3.4 Hz), 3.47 (3H, s), 3.81 (3H, s), 4.30 (1H, s); 13C NMR (75 MHz) delta 13.7, 22.2, 22.5, 31.0, 38.4, 52.5, 58.5, 86.6, 167.5, 203.9.; numax (neat) / cm-1 2955, 1750, 1726, 1438, 1402, 1272, 1203, 1119; HRMS (ESI) calcd for C10H18O4 (M+Na+) 225.1103, found 225.1109.

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; Ashida, Yuichiro; Sato, Yuka; Honda, Atsushi; Nakatsuji, Hidefumi; Tanabe, Yoo; Synthesis; vol. 48; 23; (2016); p. 4072 – 4080;,
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. 98545-64-3, name is Methyl 4-amino-2-bromobenzoate, A new synthetic method of this compound is introduced below., name: Methyl 4-amino-2-bromobenzoate

To a solution of 4-amino-2-bromobenzoic acid methyl ester (1700 mg, 7.368 mmol) in concentrated hydrochloric acid (27 mL) and water (102 mL) was added dropwise a solution of sodium nitrite (567 mg, 8.104 mmol) in water (25 mL) at -5C, and the mixture was stirred at -5C for 30 minutes. To the reaction mixture was added dropwise a solution prepared in (1-A) at -5C, the reaction temperature was gradually elevated, and the mixture was stirred at room temperature for 2 hours. The obtained viscous material was collected by filtration, the obtained viscous material was dissolved in chloroform, dried, and concentrated under reduced pressure. The obtained residue was purified by a silica gel column chromatography (hexane:ethyl acetate = 100:0?60:40) to give methyl 2-bromo-4-(chlorosulfonyl)benzoate (997 mg, 43%) as an orange solid. 1H-NMR (DMSO-d6) delta 3.86 (3H, s), 7.66 (1H, dd, J = 1.5 Hz, 7.9 Hz), 7.76 (1H, d, J = 7.9 Hz), 7.84 (1H, d, J = 1.5 Hz).

The synthetic route of 98545-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; KATO, Taku; SAKAMOTO, Toshiaki; KUBO, Akira; SAWAMOTO, Daisuke; EP2896613; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 106614-28-2, name is Methyl 2,4-difluorobenzoate, 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 106614-28-2, Application In Synthesis of Methyl 2,4-difluorobenzoate

Step 2; Preparation of 2-fluoro-4-(4-metriotayl-piperazm-1-yl)-benzolc acid methyl ester and 4-fluoro-2-{4-methyl-pfpeFazin-1-yl}-benzoic acid methyl ester; A mixture of 2,4-difluoro-benzoic acid methyl ester (4 5 g, 26,2 mmol), 1-methyi- piperazine (4 36 mL, 39,2 mmol, 1.5 eq.) and K2CO3 (3,62 g, 26.2 mrno), 1 eq.) in N1N- dlmethylformamide (10 mL) was stirred at 100C for 4 hours. The mixture was then poured into 200 mL of water and extracted with 150 mL of EtOAc. The organic layer was separated, washed with water (100 mL) dried over sodium sulphate and evaporated to dryness. The crude was purified by flash chromatography on silica gel, using a mixture dichloromethane- MeOH-30% NH4OH 95:5:0 5 as eluant, affording 1 65 g of 2-fluoro-4-(4-rnethyi-piperazin-1-yl)- benzoic acid methyl ester (first eluting, pale yeilow solid) and 3.04 g of 4-fluoralpha-2-(4-methyl- piperazin-1-yl)-benzoic acid methyl ester (second eiuting, yellow oil).

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 2,4-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER ITALIA S.R.L.; WO2007/99171; (2007); A2;,
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. 69038-74-0, name is tert-Butyl 3-Bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H13BrO2

Example 36E tert-butyl 5′-amino-2′-methyl[1,1′-biphenyl]-3-carboxylate A mixture of 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.00 g, 19.8 mmol) and tert-butyl 3-bromobenzoate (5.08 g, 19.8 mmol) in 1,4-dioxane (110 mL) and water (30 mL) was degassed under a N2 flow for 40 minutes. Potassium carbonate (13.7 g, 99 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (816 mg, 1.00 mmol) were added, and the mixture stirred at 80° C. for 7 hours. Water was then added to the reaction mixture, and it was extracted with ethyl acetate (2*). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography using a Biotage® SNAP 340 g silica column, eluted with 10-25percent ethyl acetate in iso-hexane, to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.97-7.93 (m, 2H), 7.49-7.41 (m, 2H), 7.06 (d, J=8.0 Hz, 1H), 6.64 (dd, J=2.4, 8.0 Hz, 1H), 6.60 (d, J=2.4 Hz, 1H), 3.60 (broad s, 2H), 2.14 (s, 3H), 1.60 (s, 9H).

According to the analysis of related databases, 69038-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); 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. 1559-02-0, name is Diethyl 1,1-cyclopropanedicarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H14O4

(a) 1-Ethoxycarbonylcyclopropanecarboxylic acid (1a) A solution of sodium hydroxide (2.15 g, 54 mmol) in water (15 ml) was added dropwise to a stirred solution of diethyl 1,1-cyclopropanedicarboxylate (10 g, 54 mmol) in ethanol (30 ml) while the temperature was maintained below 25 C. After the completion of the addition, the resulting mixture was stirred at room temperature for 60 hours. Most of ethanol was removed by evaporation in vacuo and the residue was diluted with brine, acidified with 6N hydrochloric acid and extracted with diethyl ether. The extract was dried over magnesium sulfate, filtered and concentrated. The residue was purified by distillation to give the title compound (bp 66-9 C./0.15 mm) as a viscous oil.

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 1559-02-0.

Reference:
Patent; Merck & Co., Inc.; US4766145; (1988); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics