Author: Jessica.F

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. 90971-88-3, name is Methyl 2-bromo-5-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 2-bromo-5-methylbenzoate

Example 15; Synthesis of 5-methyl-2-triisopropylsilanylsulfanyl-benzoic acid methyl ester (Method 15.) 2-Bromo-5-methyl-benzoic acid methyl ester (2.06 g, 9.00 mmol), tris(dibenzylideneacetone)dipalladium (0) (83 mg, 0.09 mmol), bis(2-diphenylphosphinophenyl)ether (97 mg, 0.18 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), triisopropylsilanethiol (1.37g, 7.2 mmol) and dry toluene (10 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 150 C. for 30 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (2:8). This furnishes the title compound as an oil, which is used in the next step without further purification.

The synthetic route of 90971-88-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kehler, Jan; Juhl, Karsten; Norgaard, Morten Bang; US2006/287386; (2006); A1;,
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Electric Literature of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

A solution of MeCN (1 mmol) containing chromene diene 13 (0.5 mmol) and the corresponding enamino ester 9 or? -enaminokone 11 (0.6 mmol) shown in Table 1 3.0 mL) was stirred at room temperature while adding indium (III) trifluoromethanesulfonate [Indium (III) trifluoromethanesulfonate].The reaction mixture was stirred for 2-8 hours, and after completion of the reaction was confirmed by TLC (hexane-EtOAc, 4: 1, v / v), 10 mL of water was added and the solution was extracted with ethyl acetate (10 mL x 3) .The solvent was evaporated and the residue was subjected to silica gel column chromatography using hexane-ethyl acetate (4: 1, v / v) to obtain the following compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-(dimethylamino)acrylate, its application will become more common.

Reference:
Patent; Yeungnam University Industry-Academic Cooperation Foundation; Lee Yong-rok; (31 pag.)KR2018/3669; (2018); A;,
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Electric Literature of 17449-48-8,Some common heterocyclic compound, 17449-48-8, name is Dimethyl 5-fluoroisophthalate, molecular formula is C10H9FO4, 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.

Concentrated [HC1] (30 ml) was added to a cooled [(-5C)] suspension of dimethyl 5-amino isophthalate (20 g, 95.6 mmol) in water (75 ml), followed by portionwise addition of [NAN02] (7.5 g, 109 mmol). The reaction mixture was then stirred for 15 min. , after which [HBF4 (18] ml, 100 mmol, 48% aqueous solution) was added. The resulting mixture was stirred at [0C] for 30 min. and the precipitate formed was collected by filtration and washed with cold methanol (60 ml) and ether (60 ml). The residue was then decomposed by heating in an oil bath [(~110C).] The cooled mixture was then diluted with ether, concentrated onto silica gel and purified by flash chromatography with 5% ethyl acetate hexane as eluant giving 9.0 g (44%) of product as a white fluffy [SOLID. LH NE (CDC13), 6] [(PPM)] : 8.57 (s, 1H), 7.95 (d, 2H), 3.97 (s, 6H). A suspension of 5-fluoro-isophthalic acid dimethyl ester (1.7 g, 8. 0 mmol) in methanol (41 ml) was treated with 1.0 N sodium hydroxide (7.2 ml, 7.2 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1.0 N [HC1] to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulphate. After removal of solvent in vacuo, a total of 1.3 g (83%) of 5-fluoro-isophthalic acid monomethyl ester was isolated as a white [SOLID. LH] NMR (DMSO), [5] (ppm): 8.31 (t, 1H), 7.96 (m, 2H), 3.91 (s, 3H). Triethylamine (2.2 ml, 16.0 mmol) and isobutyl [CHLOROFORMATE] (1.0 ml, 8. 0 mmol) were added to an ice-cooled solution [OF 5-FLUORO-ISOPHTHALIC] acid monomethyl ester (1.3 g, 6.7 mmol) in dichloromethane (20 ml) and then warmed to room temperature. After stirring for 2 h, the reaction mixture was filtered and concentrated. The residue was re-dissolved tetrahydrofuran (10 ml) and then sodium borohydride [(1.] 1 g, 29.02 mmol) in water (3ml) was added drop-wise. After 1 h, the reaction was quenched with methanol and then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Flash column chromatography on silica gel using 30% ethyl acetate in hexanes afforded 667 mg (54%) of 3-fluoro-5-hydroxymethyl-benzoic acid methyl ester as a colorless [OIL. 1H] NMR [(CDC13),] [8] (ppm): 7.82 (s, 1H), 7.63 (d, 1H), 7.32 (d, 1H), 4.76 (s, 2H), 3.93 (s, 3H). Ethanol (2 ml) was added to round bottom flask containing 3-fluoro-5-hydroxymethyl- benzoic acid methyl ester (667 mg, 3.6 mmol) and palladium (10 wt. % on activated carbon, 300 mg) under argon. The flask was evacuated using a water aspirator and then filled with hydrogen from a balloon. After stirring for 2 h, the palladium on carbon was removed by filtration through celite. The filtrate was then concentrated to afford 520 mg (87%) of 3-fluoro-5-methyl-benzoic acid methyl [ESTER. LH] NMR [(CDC13),] 8 (ppm): 7.65 (s, 1H), 7.51 (d, 1H), 7.08 (d, 1H), 3.91 (s, 3H), 2.40 (s, 3H). 0.5 N Lithium hydroxide (7.4 ml, 3.7 mmol) was added to a solution 3-fluoro-5-methyl- benzoic acid methyl ester (520 mg, 3.1 mmol) in tetrahydrofuran (7.4 ml). The reaction was stirred at [75 C] for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH about 2) by the addition of 10% [HC1] (aq. ). Following extraction of the aqueous layer with ethyl acetate, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 469 mg (98%) [OF 3-FLUORO-5-METHYL-BENZOIC] acid as a white solid. 1H NMR (DMSO), d (ppm): 7.62 (s, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 2.38 (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 Dimethyl 5-fluoroisophthalate, its application will become more common.

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
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These common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, 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: C5H9BrO2

To a solution of CH3ONa (587.78 mg, 10.88 mmol, 1.0 eq) in MeOH (20.0 mL) was addedmethyl 2-bromo-2-methyl-propanoate (1.97 g, 10.88 mmol, 1.41 mL, 1.0 eq) and tert-butyl Nhydroxy-N-methyl-carbamate (1.60 g, 10.88 mmol, 1.0 eq) at 15 C. The mixture was heated to 60 C with stirring for 16 h. TLC (PE: EtOAc = 5:1) showed that starting material was consumed completely and one main new spot formed. The mixture was evaporated to removethe solvent and get the residue. The residue was purified by column chromatography (5i02,Petroleum ether/Ethyl acetate=l0/l to 20/1) to obtain the title 0 (2.30 g, 9.30 mmol,85.49% yield) as off-white liquid. ?H NIVIR (4001V11{z, CHLOROFORM-d) = 3.74 (s, 3 H),3.11 (s, 3 H), 1.48 (d,J=4.9Hz, 15 H).

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

Reference:
Patent; NOVIRA THERAPEUTICS, INC.; KUDUK, Scott; HARTMAN, George, D.; (433 pag.)WO2018/5881; (2018); A1;,
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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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

To available thiophen-3-ylamine 2p1 (0.50 g, 5.04 rnmol) was added imidate2g2 (1.08g, 5.5mmol) in ethanol (10 mL) under a N2 atmosphere. The mixture wasstirred at R.T. for 3 h at which point the reaction was concentrated. To the residuewas added ether, and the suspension filtered and washed with ether to afford adduct2p2(1.0g, 82percent). This material was sufficiently clean to be used in the subsequentstep. MS: 242.1 (MH)+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 4891-38-7, name is Methyl Phenylpropiolate, 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 4891-38-7, category: esters-buliding-blocks

General procedure: A reaction kettle (30 mL) was charged with aniline (1.0 mmol), and alkyne ester (1.0 mmol). The mixture was stirred at room temperature for 10 minutes, then added terminal alkyne (1.2 mmol, 1.2 eq), AgOTf (5 mol%, 12.9 mg), HOTf (10 mol%, 15 mg), MeOH (2 mL) in the mixture. The mixture was stirred at 120 oC for 24 hours, the mixture was quenched by sat. aq. NaHCO3, and diluted with 20 mL of dichloromethane and washed with 10 mL of H2O. The aqueous layer was extracted twice with dichloromethane (10 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents, the residue was purified by silica gel chromatography (hexane/AcOEt = 5:1) to afford quinoline derivatives. All other compounds are synthesized in a similar manner, with the yields listed in the main text calculated from the isolated, pure products.

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

Reference:
Article; Li, Yunlan; Zhang, Qiurui; Xu, Xuefeng; Zhang, Xu; Yang, Yurong; Yi, Wei; Tetrahedron Letters; vol. 60; 14; (2019); p. 965 – 970;,
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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. 40637-56-7, name is Dimethyl 2-allylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H12O4

According to a reported procedure,18 a solution of dimethyl 2-allylmalonate (19) (1.77 mL, 11.0mmol, 1.0 equiv) in Et2O (25 mL) was added dropwise to a suspension of LiAlH4 (1.25 g, 33.0mmol, 3.0 equiv) in Et2O (31 mL) at 0C. The resulting mixture was stirred at room temperature for3 h; it was then cooled back to 0C and the reaction was quenched by slow addition of water (1.05mL). The mixture was allowed to warm to rt and treated with aqueous NaOH (15%, 1.05 mL) andwater (3.2 mL). The resulting white slurry was filtered through Celite and then washed with EtOAc(4 x 50 mL). After removal of the solvent by distillation under reduced pressure, the crude productwas purified by column chromatography (SiO2, eluting with Et2O) to afford diol 20 as a colorlessoil (744 mg, 6.40 mmol, 58% yield). Following a reported procedure,19 a solution of diol 20 (581 mg, 5.00 mmol, 1.0 equiv) in THF (4.0mL) was added dropwise to a suspension of NaH (60% dispersion in mineral oil, 120 mg, 5.00mmol, 1.0 equiv) in THF (10 mL). The mixture was stirred at rt for 50 min and then a solution oftriisopropyl silyl chloride (0.96 mL, 4.5 mmol, 0.9 equiv) in THF (4.0 mL) was slowly added. Afterstirring for 2 h, the reaction was quenched by treatment with aqueous K2CO3 (1.0 M, 15 mL). Theaqueous layer was separated from the organic one and extracted with Et2O (3 x 15 mL). Thecombined organic layers were washed with brine (15 mL), dried over MgSO4, filtered and thesolvent was removed in vacuo. Purification by column chromatography (SiO2, eluting with 95:5pentane:EtOAc) afforded the monoprotected diol 21 as a colorless oil (1.15 g, 4.23 mmol, 85%yield).

The synthetic route of 40637-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nicolai, Stefano; Swallow, Peter; Waser, Jerome; Tetrahedron; vol. 71; 35; (2015); p. 5959 – 5964;,
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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. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 18595-14-7

Into a 500-mL round-bottom flask was placed a solution of methyl 4-amino-3-methylbenzoate (4.00 g, 24.2 mmol, 1.00 equiv) and NaSCN (7.00 g, 86.4 mol, 3.57 equiv) in AcOH (90 mL) that was cooled to 0 C. This was followed by the addition of a solution of Br2 (3.9 g, 25 mmol, 1.0 equiv) in AcOH (25 mL) dropwise, maintaining at 0 C over 20 min. The resulting solution was allowed to warm to RT on its own accord (over approximately 10 min.) and stirred for 48 hrs at RT. At this time, the solids of the reaction were filtered out. The resulting solution was diluted with 100 mL H20. The pH value of the solution was adjusted to 8-9 with ammonia (using Whatman PH strip paper to monitor PH adjustment) which furnished an immediate precipitation. The solids were collected by filtration and washed once with ice cold MeOH (50 mL) to afford as a yellow solid. MS m/z 223.0 (M+l). 1H NMR (400 MHz, MeOH- 4) delta 8.17 (app d, J = 1.0 Hz, 1H), 8.03 (br s, 2H, NH2), 7.68 (s, 1H), 3.82 (s, 3H), 2.42 (s, 3H).

According to the analysis of related databases, 18595-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; TULLY, David C.; RUCKER, Paul Vincent; ALPER, Phillip B.; MUTNICK, Daniel; CHIANELLI, Donatella; WO2012/87519; (2012); A1;,
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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 35418-07-6 as follows. Computed Properties of C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

According to the analysis of related databases, 35418-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H13NO2

The appropriate amino acid derivative from Example 9 (0.020 g, 0.05 mmol) was dissolved in DCM (1 mL). DMAP (0.018 g, 3 equivalents), Et3N (20 muL, 0.15 mmol, 3 equivalents), BroP (0.058 g, 0.15 mmol, 3 equivalent), and ethyl-4-aminocinnamate (0.029 g, 0.015 mmol, 3 equivalents) were added and the mixture stirred for 20 h at room temperature. Camphor-10-sulfonic acid (CSA; 0.046 g, 0.2 mmol, 4 equivalents) was added and the reaction mixture was stirred for an additional 24 h at room temperature.

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 5048-82-8.

Reference:
Patent; Boehringer Ingelheim (Canada) Ltd.; US2003/236251; (2003); A1;,
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