Month: March 2021

Reference of 801282-00-8, These common heterocyclic compound, 801282-00-8, name is 2-Fluoro-3-methoxyaniline, 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.

00157] Preparation of compound 10[00158] To a solution of compound 9 (13 g, 92 mmol) in DMF (100 mL) was added a solution of NBS (16.4 g, 92 mmol, 1.0 eq) in DMF (100 mL) drop-wise. The reaction mixture was stirred at room temperature for 3h, then diluted with ethyl acetate (500 mL) and washed with brine (2xl50mL). The organic phase was dried (Na2S04), filtered and concentrated to give the title compound 10 as brown oil (23 g, 98% yield). ESI-MS (M+H) : 219.9.

Statistics shows that 2-Fluoro-3-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 801282-00-8.

Reference:
Patent; SUZHOU KINTOR PHARMACEUTICALS,INC.; TONG, Youzhi; WO2012/119559; (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 456-49-5 as follows. Recommanded Product: 1-Fluoro-3-methoxybenzene

To a solution of n-butyllithium (2.6 M, n-hexane solution, 12.7 mL, 33 mmol) dissolved in THF (100 mL) was addeddropwise a solution of 3-fluoroanisole (3.44 mL, 31.1 mmol) dissolved in THF (10 mL) at -78 C. After stirring for 10min at the same temperature, to the mixture was added dropwise a solution of iodine (9.14 g, 36.0 mmol) dissolved inTHF (60 mL) at -78 C. After stirring for 30 min at the same temperature, to the mixture were added aqueous saturatedammonium chloride (20 mL) and then aqueous saturated sodium thiosulfate (40 mL). The mixture was extracted withn-hexane (20 mL ¡Á 3), and the combined organic extract was washed with brine (20 mL), dried (Na2SO4), and afterfiltration, the filtrate was concentrated under reduced pressure. The residue was purified by flash columnchromatography (silica-gel 156 g, n-hexane/EtOAc = 5/1) to give 3-fluoro-2-iodoanisole (7.03 g, 27.9 mmol, 93.0%) asa colorless oil.

According to the analysis of related databases, 456-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yoshida, Suguru; Nagai, Akira; Uchida, Keisuke; Hosoya, Takamitsu; Chemistry Letters; vol. 46; 5; (2017); p. 733 – 736;,
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Reference of 458-03-7, A common heterocyclic compound, 458-03-7, name is 1-Ethoxy-3-fluorobenzene, molecular formula is C8H9FO, 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.

2- (3-Ethoxy-phenyl)-2-methyl-propionitrile was prepared using a procedure adapted from literature (Organic Syntheses, Vol. 79, pp. 209-215). To a solution of 1-ethoxy-3-fluoro benzene (3.0 g, 19.4 mmol) in 25 mL of toluene was added solid potassium bis (trimethylsilyl)amide (5.84g, 29.2 mmol, 1.5 eq) followed by isobutyronitrile (7.08 mL, 77.8 mmol, 4 eq). The reaction mixture was stirred at 100 C for 12 hr. It was diluted with 75 mL of ethyl acetate and 75 mL of IN aqueous hydrochloric acid. The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water (1 x 50 mL), brine (1 x 50 mL), and dried over anhydrous magnesium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo. The residue was dissolved in 5 mL of methylene chloride and applied to a 40 g silica gel cartridge. The product was eluted using a gradient of ethyl acetate in hexanes to yield 2.96 g (15.6mmol, 80%) of pure 2-(3-ethoxy- phenyl) -2-methyl-propionitrile. LR-MS: 190.12 [(M+H)+] 2- (3-Ethoxy-phenyl)-2-methyl-propionitrile (2.96 grams, 15.65 mmol) was dissolved in a freshly prepared acetic acid solution of iodine monochloride (20 mL of a 1.54 M iodine monochloride solution in acetic acid, 30.8 mmol). The reaction was slightly exothermic. The reaction mixture was allowed to stand at room temperature for 3 d. The reaction mixture was concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 10% sodium carbonate (1x), brine (1x), and dried (anhydrous magnesium sulfate). The solids were filtered off, and the filtrate was concentrated to dryness. The residue was purified by flash chromatography (110 g of silica gel, eluting with a gradient of ethyl acetate in hexanes) to give 2- (3-ethoxy-4-iodo-phenyl)-2-methyl-propionitrile g, 51%). LR-MS: 316.21 [(M+H)+] Nitrogen gas was bubbled through a solution of (3-ethoxy-4-iodo-phenyl)-2-methyl- propionitrile (2.53 grams, 8 mmol) and diisopropylethylamine (2.09 mL, 12 mmol) in methanol (10 mL). Using a balloon filled with carbon monoxide gas (CO) and equipped with a needle, CO was bubbled through the mixture until it was saturated. Palladium (II) acetate (100 mg) was added, and the mixture was stirred under an atmosphere of CO at 60 C for 6 d. The reaction mixture was filtered and concentrated. The residue was partitioned between methylene chloride and 1.0M hydrochloric acid. The organic layer was dried (anhydrous magnesium sulfate), filtered. The residue was purified by flash chromatography (120 g of silica gel, eluting with a gradient of ethyl acetate in hexanes) to give methyl 4-(cyano-dimethylmethyl)-2-ethoxy- benzoate (1.09 g, 55%). LR-MS: 248.19 [(M+H)@]

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; F.HOFFMANN-LA ROCHE AG; WO2005/110996; (2005); A1;,
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Application of 107622-80-0, 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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The appropriate pyrazole (1.0 equiv) was treated with phosgene(20% in toluene) at 0 C. The reaction mixture was stirred at room temperature for 1 h.The solvent was removed under reduced pressure and the crude carbamoyl chloride was redissolved in anhydrous CH2Cl2 (0.5 M). The appropriate amine (1.0 equiv) and Et3N (1.2 equiv) were dissolved in CH2Cl2 and cooled to 0 C. The crude carbamoyl chloride was added dropwise and the reaction mixture was stirred at room temperature for 16 h.The mixture was diluted with EtOAc, washed with saturated aqueous NaCl, and dried over Na2SO4. Evaporation under reduced pressure yielded the crude coupling product that was purified by flash chromatography (SiO2).

The synthetic route of (4-Phenoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Otrubova, Katerina; Srinivasan, Venkat; Boger, Dale L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3807 – 3813;,
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Application of 39538-68-6, 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. 39538-68-6, name is 2-Methoxy-4-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Malonyl diamide derivatives were prepared as described earlier.49 Briefly: To a magnetically stirred ice bath-cooled solution of the selected amine (14 mmol), and triethylamine (14 mmol, 1.4 g) in dioxane (20 ml), malonyl dichloride (1.0 g, 7.0 mmol) solution in dioxane (20 ml) was added dropwise over 15 min. The reaction mixture was stirred at 0 C for one hour. Subsequently, HCl (2 N, 50 ml) was added to the reaction suspension and stirred for 30 minutes. Finally, the mixture was filtered to afford the products as whitish to gray solids that were further washed by stirring in water (50 mL) for 30 min (Scheme 1).

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

Reference:
Article; Habash, Maha; Taha, Mutasem O.; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4746 – 4771;,
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These common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, 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. Recommanded Product: 7252-83-7

(1) Synthesis of 1-(2,2-Dimethoxyethylsulfanyl)-4-fluorobenzene In a nitrogen stream, 4-fluorobenzenethiol (2.5 ml, 23.4 mmol) and 2-bromo-1,1-dimethoxyethane (3.0 ml, 25.7 mmol) were added to a sodium methoxide methanol solution (0.5 M, 74.9 ml, 37.4 mmol) under cooling with ice and the reaction mixture was stirred at the same temperature for 10 minutes, and then heated and refluxed for five hours. The reaction mixture was concentrated under reduced pressure, and added with cold water. The mixture was extracted with ether. The organic layer was washed with a saturated sodium chloride aqueous solution, and then dried with sodium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate: n-hexane (1:20)] to obtain the title compound (4.52 g, 89%). 1H-NMR (CDCl3) delta: 3.05 (2H, d, J=5.4 Hz), 3.35 (6H, s), 4.49 (1H, t, J=5.4 Hz), 6.85 (2H, t, J=9.0 Hz), 7.31 (2H, dd, J=8.7, 5.1 Hz)

The synthetic route of 2-Bromo-1,1-dimethoxyethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1803721; (2007); 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, A new synthetic method of this compound is introduced below., COA of Formula: C5H11BrO2

0.058 mmol of hydroxystyrene was put into a 500 ml round-bottom flask, 50 ml of acetonitrile was added thereto to dissolve the hydroxystyrene, and then 0.07 1 mol ofpotassium t-butoxide was added dropwise to the flask, and the resulting solution was refluxed for 1 hout Subsequently, 0.076 mol of 1 -bromo-2-(2-methoxyethoxy)ethane was slowly added dropwise to the resultant and then refluxed in a nitrogen atmosphere for 6 hours to allow a reaction to occur therebetween. Afier the reaction was completed, the reaction product was neutralized with an aqueous hydrochloric acid solution, and then an organic layer was extracted with ethyl acetate/a saturated aqueous solution of a base, and the organic layer was dried with anhydrous magnesium sulfate and filtered to remove any remaining moisture. Thereafter, the solvent was removed under reduced pressure and, as a result, 10 g (96%) of a title compound represented by Formula (ii) below was obtained as a pale brown liquid. ?H NMR spectroscopic data of the purified 1 -(2-(2-methoxyethoxy)ethoxy)-4-vinylbenzene (ii) is as follows:

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Kim, Min Soo; Choi, Won Mun; Joe, Dae June; (13 pag.)US2018/244819; (2018); 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 109-85-3 as follows. Formula: C3H9NO

Ligand 1b was prepared according to the method described for 1a using 2-(methoxy)ethylamine (0.39 mL, 4.54 mmol) and 1- methyl-1H-imidazole-2-carbaldehyde (0.455 g, 4.13 mmol) and isolated as a pale yellow oil in 92% yield. 1H NMR (300 MHz, CD2Cl2): d(ppm) 8.26 (s, 1H), 7.04 (s, 1H), 6.94 (s, 1H), 3.95 (s, 3H), 3.75e3.68 (m, 2H), 3.67e3.60 (m, 2H), 3.33 (s, 3H). 13C{1H} NMR (75 MHz, CD2Cl2): d(ppm) 154.96, 143.59, 129.32, 125.12, 72.53, 61.64, 58.86, 35.46. FT-IR (cm 1): 2875m, 1650s (nC]N), 1518w, 1475m, 1437m, 1366w, 1287m, 1236w, 1191w, 1118s, 1026w, 955w, 919m, 802m, 757m, 708m, 690m, 558w, 473w.

According to the analysis of related databases, 109-85-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Boudier, Adrien; Breuil, Pierre-Alain R.; Magna, Lionel; Olivier-Bourbigou, Helene; Braunstein, Pierre; Journal of Organometallic Chemistry; vol. 718; (2012); p. 31 – 37,7;; ; Article; Boudier, Adrien; Breuil, Pierre-Alain R.; Magna, Lionel; Olivier-Bourbigou, Helene; Braunstein, Pierre; Journal of Organometallic Chemistry; vol. 718; (2012); p. 31 – 37;,
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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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C13H11BrO

Benzylation of 3-bromophenol 1 with benzyl chloride and potassium carbonate in DMF affords compound 2. Palladium (0)-catalyzed cross-coupling reaction of 2 with bis(pinacolato)diboron, PdCl2(dppf), and potassium carbonate in DMSO at 80 C. gives rise to compound 3 (Ishiyama, T; Murata, M; Miyaura, N. J. Org. Chem. 1995, 60, 7508). Debenzylation of 3 with Pd/C at 60 psi hydrogen in MeOH produces the target compound 4 (Pennington, T. E.; Kardiman, C; Hutton, C. A. Tetrahedron Lett. 2004, 45, 6657).

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 53087-13-1.

Reference:
Patent; The Procter & Gamble Company; US2007/209123; (2007); A1;,
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Application of 14804-31-0,Some common heterocyclic compound, 14804-31-0, name is 4-Bromo-1-methoxy-2-methylbenzene, molecular formula is C8H9BrO, 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.

Reference Example 595-[4-(4-methoxy-3-methylphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-oneSodium t-butoxide (999 mg, 10.4 mmol) was added to a mixture of toluene (18 mL) containing 2,2,4,6,7-pentamethyl-5-piperazin-1-yl-1-benzofuran-3(2H)-one (1.00 g, 3.47 mmol) synthesized in Reference Example 58, 4-bromo-2-methylanisole (2.09 g, 10.4 mmol), palladium acetate (39 mg, 0.174 mmol) and BINAP (325 mg, 0.522 mmol), and the mixture was stirred under heated reflux for 15 hours. After cooled to room temperature, the reaction solution was diluted with water and extracted using ethyl acetate. The organic layer was washed with saturated saline, and then dried using anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5 to 85:15). Crystallization was performed using ethyl acetate-hexane to give 320 mg of the title compound (yield: 23%).Melting point: 129-131 C.1H-NMR (CDCl3): delta1.43 (6H, s), 2.18 (3H, s), 2.22 (3H, s), 2.35 (3H, s), 2.61 (3H, s), 3.02-3.42 (8H, m), 3.80 (3H, s), 6.74-6.84 (2H, m), 6.85-6.89 (1H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-1-methoxy-2-methylbenzene, its application will become more common.

Reference:
Patent; Tsukamoto, Tetsuya; Wakabayashi, Takeshi; Ohra, Taiichi; US2010/234357; (2010); A1;,
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