Month: May 2021

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. 53088-68-9, name is Methyl (3-Chlorophenyl)acetate, A new synthetic method of this compound is introduced below., Formula: C9H9ClO2

REFERENCE EXAMPLE 30 Methyl (RS)-a-bromo-(3-chlorophenyl)acetate A mixture of Reference Example 29 (5.0 g), N-bromosuccinimide (5.3 g) and azobisisobutyronitrile (0.38 g) in dry chloroform (50 ml) was heated at reflux for 6 hours. The reaction mixture was washed four times with water (50 ml) and the organic phase dried over magnesium sulphate and evaporated. The residual oil was purified by flash chromatography on silica eluding with a mixture of ethyl acetate and pentane (5:95, v/v). Fractions homogenous in the required product were combined and evaporated to give the title compound (4.3 g) as an 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; Rhone-Poulenc Rorer Limited; US6048893; (2000); A;; ; Patent; Rhone-Poulenc Rorer Limited; US6124343; (2000); A;,
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Electric Literature of 69038-74-0, These common heterocyclic compound, 69038-74-0, name is tert-Butyl 3-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.

(+)-Pinanediol 3-(teri-butoxycarbonyl)benzeneboronate (12b). A solution of tert- butyl 3-bromo-benzoate (1.70 g, 6.61 mmol), obtained from 3-bromobenzoic acid, (Wright, S. W. et al, Tetrahedron Lett. 1997, 38, 7345-7348) and freshly distilled triisopropyl borate (1.53 mL, 6.61 mmol) in THF (17 mL) was cooled to -100 °C under argon flow and w-butyllithium (2.5 M soln in hexane, 2.91 mL, 7.27 mmol) was added dropwise over 15 min, during which the solution turned cherry red. After 1 h at -100 °C, trimethylsilyl chloride (0.84 mL, 6.61 mmol) was dropped into the reactor and the resulting colorless solution was allowed to warm to room temperature and stirred overnight. Finally, (+)-pinanediol (1.12 g, 6.61 mmol) was added and the solution stirred 1 h at room temperature. The mixture was partitioned between ethyl acetate (100 mL) and water (40 mL) and the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The combined organic phases were washed with brine, dried over MgS04, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (light petroleum/ethyl ether 95:5), affording 12b as a yellowish solid (2.10 g, 89percent yield). Mp 70-71 °C. [CC]D +7.3 (c 1.1, CHCI3). XH-NMR (400 MHz, CDC13): delta 0.94 (3H, s, pinanyl CH»), 1.24 (1H, d, J 10.9, pinanyl Hendo), 1.36 (3H, s, pinanyl G¾), 1.53 (3H, s, pinanyl CH3), 1.64 (9H, s, f-Bu), 1.98-2.30 (5H, m, pinanyl protons), 4.51 (1H, dd, J 8.5, 2.0, CHOB), 7.46 (1Eta, t, J7.6, ¾), 8.0 (1Eta, d, J 7.6, H4), 8.12 (1H, d, J7.6, H6), 8.45 (1H, s, H2). 13C-NMR (100 MHz, CDCI3): delta 24.0, 26.5, 27.1, 28.2, 28.7, 35.5, 38.2, 39.5, 51.4, 78.4, 80.9, 86.5, 127.6, 131.5, 132.1, 135.7, 138.7, 169.5, CB not seen. EI-MS: m/z 356 (M+, 10percent), 300 (36), 283 (41), 231 (50), 204 (38), 83 (65), 67 (59), 57 (100). Anal. Calcd. for C2iH29B04: C, 70.80; H, 8.20. Found: C, 70.55; H, 8.22.

The synthetic route of 69038-74-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI MODENA E REGGIO EMILIA; SHOICHET, Brian K.; PRATI, Fabio; CASELLI, Emilia; ROMAGNOLI, Chiara; EIDAM, Oliv; WO2013/56163; (2013); A1;,
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Synthetic Route of 3195-24-2, These common heterocyclic compound, 3195-24-2, name is Diethyl 2,2-diallylmalonate, 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.

General procedure: In a 10 mL tube, the supported catalyst (0.002 mmol Ru) was dried for 1 h under vacuum (1.0 mbar). Then a solution of diene (0.1 mmol) in dry and degassed solvent (1 mL) was transferred via a cannula to the tube containing the catalyst under argon. The resulting suspension was stirred at the target temperature and the conversion was monitored by GC until the end of the experiment. At this time, the stirring was stopped, the material was left to settle and the solution was filtered via a cannula under nitrogen. The recovered catalyst was washed with dry and degassed solvent (3×3 mL), dried under vacuum and directly used in the next cycle. The filtrates were concentrated under reduced pressure to afford the corresponding RCM product, whose yield was determined by 1H NMR spectroscopy.

The synthetic route of 3195-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Monge-Marcet, Amalia; Pleixats, Roser; Cattoen, Xavier; Wong Chi Man, Michel; Tetrahedron; vol. 69; 1; (2013); p. 341 – 348;,
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Synthetic Route of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 72 (2S)-1-({1-[2-(3-Chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-cyclopropylamino}-acetyl)-pyrrolidine-2-carbonitrile The title compound was prepared in analogy to example 60 starting from 4-chloromethyl-5-methyl-2-(3-chloro-phenyl)-oxazole and tert.butyl cyclopropanecarboxylate. The starting material could be prepared from 3-methylbenzaldehyde and 2,3-butanedione oxime as described for benzaldehyde in Chem. Pharm. Bull. 1971, 19, 2050-2057. Steps A] and C] were performed as outlined in example 60, step B] was done according to example 69. The title compound was obtained as a brown gum. MS (ISP): 399.3 (MH+) and 401.3 (MH+).

The synthetic route of tert-Butyl cyclopropanecarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer, Markus; Hunziker, Daniel; Kuehne, Holger; Loeffler, Bernd M.; Sarabu, Ramakanth; Wessel, Hans P.; US2003/130281; (2003); 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Computed Properties of C8H14O2

To a solution of 1M LDA (42.1 mmol, 42.1 mL) at – 78 C was added dropwise t-butylcyclopropane carboxylate (5.0 g, 35.1 mmol) in 70 mL THF. After 1.5 hours, a solution of allyl bromide (3.03 mL, 35.1 mmol) in 10 mL THF was added. The reaction mixture was allowed to warm slowly to room temperature. After 18 hours, the reaction was quenched with saturated NH4CI (aq), and partitioned between EtOAc and H2O. The organic and aqueous layers were separated, and the aqueous layer was washed with 2 c 20 mL ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified on an 80 g silacel column, eluting with 0-15% EtOAc/hexanes. The product fractions were concentrated in vacuo to yield 1-allyl-cyclopropanecarboxylic acid tert-butyl ester, 2.48 g (38% yield). 1H NMR (CHLOROFORM-d) d: 5.73-6.01 (m, 1H), 4.91-5.13 (m, 2H), 2.27 (dt, J=6.6, 1.3 Hz, 2H), 1.42 (s, 9H), 0.99-1.20 (m, 2H), 0.49-0.73 (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; BIOHAVEN PHARMACEUTICAL HOLDING COMPANY LTD.; CONWAY, Charles M.; DUBOWCHIK, Gene M.; PELLETIER, Jeffery Claude; REITZ, Allen B.; (186 pag.)WO2020/77038; (2020); A1;,
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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. 10076-48-9, name is Methyl 2,2-dimethoxypropanoate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H12O4

Then while still at 127 C., powdered potassium hydroxide (0.35 g, 0.006 mol) was added in one portion. There was an immediate exotherm to 135 C. In less than 40 minutes, conversion of methyl 2,2-dimethoxypropionate to methyl 2-methoxyacrylate was greater than 99%.

According to the analysis of related databases, 10076-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chevron Research Company; US4304928; (1981); A;,
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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. 583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 4-(trifluoromethyl)benzoate

General procedure: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

The synthetic route of 583-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Haifeng; Wang, Wei; Zhou, Yuan; Xia, Qin; Ren, Yanliang; Feng, Jiangtao; Peng, Hao; He, Hongwu; Feng, Lingling; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1879 – 1888;,
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Synthetic Route of 87661-20-9, These common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, 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.

Step 1-A solution of n-butyl lithium in hexane (1.4M, 16.9 mL, 0.09 mol) was added drop wise to a solution of freshly distilled diisopropylamine (3.1 mL, 0.02 mol) in dry THF (20 mL) at -60 C. under a nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (3.1 g, 0.02 mol) was added drop wise over a period of 10 min. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) above reaction mixture was added drop wise 1,8-dibromoctane (2.0 g, 7.0 mmol) in dry THF (5 mL) and DMPU (0.46 mL, 3.2 mmol). Then, the temperature was allowed to reach room temperature and stirred at the same temperature over a period of 16 hours. The resulting reaction mixture was quenched with saturated NH4Cl (50 mL) at 0 C. and the reaction mixture extracted with ether (50 mL×3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles evaporated under reduced pressure to yield a pale, yellow liquid which was filtered through a silica gel (230-400) column (1.5% ethyl acetate in pet ether) to yield 1.96 g of a crude (70%) colorless oil. The compound was taken to the next step without further purification or characterization.

The synthetic route of 87661-20-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); A1;,
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Electric Literature of 14062-29-4, 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. 14062-29-4, name is Ethyl 2-(3-chlorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of freshly prepared lithium diisopropylamide (23 mL of 0.31 M stock solution, 7.13 mmol) cooled to -78 C. was treated with (3-chloro-phenyl)-acetic acid ethyl ester (1.28 g, 6.48 mmol) in tetrahydrofuran/hexamethylphosphoramide (16.1 mL, 3:1). The resulting solution was stirred at -78 C. for 45 min. At this time, the reaction was treated with a solution of iodomethylcyclopentane (1.50 g, 7.13 mmol) in hexamethylphosphoramide (1 mL). The reaction mixture was stirred at -78 C. for 4 h. The reaction was warmed to 25 C. and stirred at 25 C. for 16 h. The reaction mixture was then quenched by the dropwise addition of a saturated aqueous ammonium chloride solution (20 mL). This mixture was poured into water (100 mL) and extracted with ethyl acetate (3*50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 75/25 hexanes/ethyl acetate) afforded 2-(3-chloro-phenyl)-3-cyclopentyl-propionic acid ethyl ester (1.70 g, 93%) as a yellow oil: EI-HRMS m/e calcd for C16H21ClO2 (M+) 280.1230, found 280.1238.

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, Ethyl 2-(3-chlorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffman-La Roche Inc.; US6610846; (2003); B1;,
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Reference of 18014-00-1, 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. 18014-00-1 name is Dimethyl 2,5-dibromoterephthalate, 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.

Example 1 Production of dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3) A mixed liquid of methyl p-dibromoterephthalate (Compound 1)(9.86 g, 28 mmol) synthesized according to the method of a literature (Macromolecules, 1999, 32, 2455), sodium 2-hexylthiophene-5-borate (Compound 2)(15.5 g, 61.6 mmol) synthesized according to the method of a literature (Org. Lett. 2006, 8, 4071), PdCl2 (dppf).CH2Cl2 (1.83 g, 2.24 mmol), and toluene (1 L) was refluxed under a nitrogen atmosphere for 9 hours. After the reaction mixed liquid was allowed to cool to room temperature, water was added to the reaction mixed liquid and the reaction mixed liquid was subjected to extraction with chloroform. The obtained organic layer was dried with sodium sulfate, and filtered, and thereafter, the solvent was distilled out under reduced pressure. The obtained mixture was separated and refined by a silica gel column chromatography to obtain dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3)(10.8 g, 20.5 mmol) in a yield of 73%. The physical properties of dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3) were as follows. 1H-NMR (CDCl3, delta ppm): 7.61 (s, 2H), 7.06 (d, 2H), 6.86 (d, 2H), 3.76 (s, 6H), 2.82 (t, 4H), 1.63-1.80 (m, 4H), 1.28-1.45 (m, 12H), 0.90 (t, 6H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl 2,5-dibromoterephthalate, and friends who are interested can also refer to it.

Reference:
Patent; Sumitomo Chemical Company Limited; US2011/87034; (2011); A1;,
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