Author: Jessica.F

Electric Literature of 1077-01-6, A common heterocyclic compound, 1077-01-6, name is 1-Fluoro-3-(trifluoromethoxy)benzene, molecular formula is C7H4F4O, 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.

Under ice cooling mixture of 3-fluoro – trifluoromethoxyphenyl (20g) was dissolved in 40 ml of concentrated sulfuric acid, with rapid stirringWas added portionwise potassium nitrate (28g), was stirred at 0oC 3 hours and stirred at room temperature overnight, the reaction solution was carefullyGo on into 1 kg ice, stirred for 30 minutes, extracted with ethyl acetate, dried over sodium sulfate, filtered, and the filtrate was evaporated, the residue was purified by column chromatography to give 12 g pale yellow liquid.

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; Shanghai Hansen Biological Pharmaceutical Co., Ltd.; Jiangsu Stockhausen Pharmaceutical Group Co., Ltd.; Sun, Xingyi; Wei, Mingsong; Cui, Yuanyuan; Tong, Chaolong; Zhang, Fujun; Bao, Rudi; Yu, Hongping; Xu, Yaochang; (41 pag.)CN105503827; (2016); A;,
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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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 588-63-6

General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 molpercent), NaI (37 mg, 0.25 mmol, 0.5 equiv), and OTMEDA (241 mg, 1.5 mmol, 3 equiv) in dry EtCMe2OH (4 mL),were added alkyl halide (0.5 mmol) and the phenylboronic acid (98mg, 0.8 mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 ¡ãC for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 ¡Á 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product( Tables 3 and 4).

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 588-63-6.

Reference:
Article; Di Franco, Thomas; Boutin, Nicolas; Hu, Xile; Synthesis; vol. 45; 21; (2013); p. 2949 – 2958;,
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Some common heterocyclic compound, 437-82-1, name is 2,6-Difluoroanisole, molecular formula is C7H6F2O, 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: 437-82-1

Example 37This example illustrates the preparation of compound 101a according to the approach provided in Scheme 31. The general method is applicable to other compounds of the present invention. In this example, Rv is H and Rw is CD3. Scheme 31Preparation of (5-bromo-2-chlorophenyl)(3,5-difluoro-4-hydroxyphenyl)- methanone (96)To a solution of 5-bromo-2-chlorobenzoic acid (3.2 g, 13.5 mmol) in dichloromethane (40 mL), oxalyl dichloride (1.7 mL, 27.1 mmol) was added. Then N, N-dimethylformamide (50 muL) was added dropwise. After the vigorous evolution of gas ceased, the mixture was stirred at 250C overnight prior to removal of the volatiles under reduced pressure. The residue was dissolved in dichloromethane (20 mL) and cooled to 0 C. Aluminum trichloride (2.7 g, 20.4 mmol) was added in portions, and the mixture was stirred for 10 minutes. Then l,3-difluoro-2- methoxybenzene (2.0 g, 13.8 mmol) was added, and the mixture was stirred at 0 0C for 2 hours. Then the reaction was allowed to warm to 25 C overnight. The reaction was quenched with ice-water (30 mL) and extracted with dichloromethane (2 x 20 mL). The combined organic layers were washed with sodium hydroxide (2 M), water, hydrochloric acid (10%), and brine prior to drying over sodium sulfate. Crude product was obtained after dichloromethane was removed under reduced pressure. The sample was dissolved in tetrahydrofuran/methanol/water (30 mL, v/v/v = 2:3:1), and lithium hydroxide monohydrate (700 mg) was added. The mixture was stirred for 1 hour at 25 0C. The solvent was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3 x 30 mL), and the extracts were washed with brine, dried over sodium sulfate, and concentrated to a crude product under reduced pressure. The residue was purified by silica column chromatography to give 1.46 g of white solid (30% yield, purity: 95%). 1H-NMR (CDCl3, 400 MHz): delta 7.59-7.62 (m, IH), 7.49-7.50 (m, IH), 7.36-7.42 (m, 3H); HPLC-MS method: Method 2, retention time 3.81 min; MS ES” (m/z): 345(M – I)”.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 437-82-1, its application will become more common.

Reference:
Patent; THERACOS, INC.; SEED, Brian; LV, Binhua; ROBERGE, Jacques, Y.; CHEN, Yuanwei; PENG, Kun; DONG, Jiajia; XU, Baihua; DU, Jiyan; ZHANG, Lili; TANG, Xinxing; XU, Ge; FENG, Yan; XU, Min; WO2010/9243; (2010); A1;,
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Synthetic Route of 592-55-2, 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 592-55-2 as follows.

To a solution of methyl 4-(hydroxymethyl)benzoate (500 mg, 3.0 mmol) and 2-bromoethyl ethyl ether (2.0 mL, 18 mmol) in dry DMF (25 mL) was added dropwise KHMDS (18 mL, 0.5 M in toluene, 9.0 mmol). After being stirred at 70 C was 2 h the mixture was treated with water and extracted with CH2Cl2. The combined organic layers were washed with brine and dried over MgSO4. After evaporation the crude product was purified by flash chromatography (hexane/EtOAc 5:1) to give 10a in 49% yield (350 mg). EI-MS: m/z 238 (M+); 1H NMR: (CDCl3, 600 MHz) delta (ppm): 1.23 (t, J = 7.0 Hz, 3H), 3.55 (q, J = 7.0 Hz, 2H), 3.61-3.67 (m, 4H), 3.91 (s, 3H), 4.64 (s, 2H), 7.42 (m, 2H), 8.01 (m, 2H); 13C NMR: (CDCl3, 90 MHz) delta (ppm): 15.2, 52.0, 66.7, 69.9, 69.9, 72.6, 127.2, 129.3, 129.7, 143.7, 167.0; IR: (NaCl) nu (cm-1): 2868, 1692, 1426, 1292, 1119, 764.

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huber, Daniela; Loeber, Stefan; Huebner, Harald; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 455 – 466;,
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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. 92248-06-1, name is Bis(3-methoxyphenyl)amine, A new synthetic method of this compound is introduced below., Product Details of 92248-06-1

EXAMPLE 5 N,N-Di(3-methoxyphenyl)-7-(benzothiazol-2-yl)-9,9-diethyl-fluoren-2-amine A mixture of 7-benzothiazol-2-yl-9,9-diethyl-2-bromofluorene (Example 4; 10.85 g, 25 mmol), 3,3′-dimethoxydiphenylamine (6.87 g, 30 mmol) and toluene (100 mL) was azeotroped dry under nitrogen and cooled. Bis(dibenzylidene acetone)palladium (0) (0.28 g, 0.49 mmol), bis(diphenylphosphino)ferrocene (0.25 g, 0.45 mmol) and sodium-t-butoxide (3.5 g, 36.4 mmol) were then added and the mixture was heated to 100 C. After 24 hours, the mixture was cooled, diluted with toluene and filtered. The filtrate was washed with water, dried and concentrated. The residue was chromatographed over silica gel. Elution with toluene-heptane (3:1) mixture gave the product, which was recrystallized from a mixture of toluene-heptane, m.p. 178-179.5 C., 11.13 g (76% yield). 1H NMR (CDCl3) delta ppm: 0.35-0.41 (t, 6H), 1.91-2.14 (m, 4H), 3.69 (s, 6H), 6.54-6.74, 7.05-7.68, 7.84-8.10 (m, 18H). 13C NMR (CDCl3) delta ppm: 8.61, 32.66, 55.18, 56.44 (sp3C), 108.62, 109.77, 116.66, 119.16, 119.42, 121.00, 121.44, 121.52, 122.94, 123.77, 124.95, 126.28, 127.28, 129.82, 131.55, 134.91, 135.61, 144.48, 147.84, 148.94, 150.67, 151.99, 154.24, 160.46, 168.81 (sp2C). Anal. Calcd for C38H34N2O2S: C, 78.33%; H, 5.88%; N, 4.81%; S, 5.49%. Found: C, 78.26%; H, 5.96%; N, 4.68%; S 5.47%.

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; The United States of America as represented by the Secretary of the Air Force; US8153812; (2012); B1;,
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Application of 1706-12-3, 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. 1706-12-3, name is 1-Methyl-4-phenoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1(b) 4-(4-Methylphenoxy)benzenesulfonyl chloride {VIII-A: Z=CH3 } To a solution of 1.84 g (10.0 mmol) of 4-methyldiphenyl ether (J. Chem. Soc., Perkin Trans. 1; 1992, 407-408) with 2 mL of dichloromethane in an ice-bath was added a solution of chlorosulfonic acid (0.73 mL, 11.0 mmol) in 2 mL of dichloromethane dropwise. The resulting mixture was stirred at 0 C. to room temperature for 2 hours, and then oxalyl chloride (11.14 mL, 13.0 mmol) was added dropwise, followed by 0.15 mL of DMF. The resulting mixture was heated to 40 C. for 1 hour and then allowed to cool to room tempereature over a 2 hour period. The reaction mixture was poured into ice-pH 7 phosphate buffer (50 mL), then extracted with EtOAc:Hexane (4:3) (3*150 mL). The combined organic layers were washed with brine (75 mL). The aqueous layer was extracted with EtOAc/Hexane(4:3) (150 mL). The organic layer was dried over Na2 SO4, then evaporated by vacuum to give crude product as white solid. This solid was triturated with hexane and collected by filtration, then dried under high vacuum to give 1.555 g (57%) of 4-(4-methylphenoxy)benzenesulfonyl chloride as white solid: mp 295-300 C.; 1 H–NMR (DMSO-d6) delta 2.34 (s, 3H), 6.91-6.99 (dd, J=7.7,8.4 Hz, 4H), 7.24-7.27 (d, J=8.4 Hz, 2H), 7.61-7.63 (d, J=8.1 Hz, 2H). Anal. calc. for C13 H11 O3 SCI: C, 55.22; H, 3.92; S, 11.34; Cl, 12.71. Found: C, 55.06; H, 3.95; S, 11.28; Cl, 12.71.

The synthetic route of 1-Methyl-4-phenoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US5985900; (1999); A;,
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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. 2252-44-0, name is 3-(Trifluoromethoxy)bromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H4BrF3O

The title compound was prepared in the manner analogous to Example 3A using 3-hydroxymethylphenylboronic acid and 1-bromo-3-trifluoromethoxy-benzene. MS m/z 251 (M-1).

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 2252-44-0.

Reference:
Patent; Auerbach, Bruce J.; Bratton, Larry D.; Filzen, Gary F.; Geyer, Andrew G.; Trivedi, Bharat K.; Unangst, Paul C.; US2003/225158; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, belongs to ethers-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 53087-13-1, HPLC of Formula: C13H11BrO

Example 66; 2-[4-[2-[5-[2-[2-benzyloxy-4-[butyl(4-hydroxybutyl)amino]phenyl]vinyl]thiophene-2-yl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile(66-1) 4-[(3-benzyloxyphenyl)butylamino]-1-butanol In 75 ml of dioxane were dissolved 5.19 g (19.7 mmol) of 3-benzyloxybromobenzene and 3.72 g (25.6 mmol) of 4-butylamino-1-butanol. To this mixture was added 5.89 g (29.5 mmol) of potassium hexamethyldisilazide and the mixture was stirred with heating at 100 C. for 22 hours. After the reaction mixture was poured into 200 ml of water, extraction with chloroform, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 2.22 g of a light brown oily matter (yield: 34.4%). 1H-NMR (600 MHz, CDCl3) delta: 0.93 (3H, t, J=7.7 Hz), 1.29-1.35 (2H, m), 1.51-1.66 (6H, m), 3.22 (2H, t, J=7.7 Hz), 3.26 (2H, t, J=7.7 Hz), 3.66 (2H, t, J=6.9 Hz), 5.05 (2H, s), 6.27-6.31 (3H, m), 7.11 (1H, t, J=8.2 Hz), 7.30-7.33 (1H, m), 7.37-7.39 (2H, m), 7.43-7.45 (2H, m)

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, 1-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otomo, Akira; Aoki, Isao; Miki, Hideki; Tazawa, Hidehisa; Yokoyama, Shiyoshi; US2012/172599; (2012); 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. 109-85-3, name is 2-Methoxyethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

EXAMPLE 532-[2-(1 ,3-benzothiazol-5-yl)-1 H-imidazol-4-yl]-1 -[2-(methyloxy)ethyl]-1 H-benzimidazole-6- carbonitrile hydrochlorideStep 1 . 5-bromo-N-[2-(methyloxy)ethyl]-2-nitroaniline: 4-bromo-2-fluoro-1 -nitrobenzene (0.3 g, 1.336 mmol), 2-(methyloxy)ethylamine (0.1 17 ml_, 1.336 mmol), and DIEA (0.238 ml_, 1 .336 mmol) in Ethanol (5 mL) were irradiated by microwave at 100C for 30 min. The reaction mixture was partitioned between dichloromethane and brine. The aqueous layer was extracted with DCM twice. The combined DCM layers were dried over sodium sulfate, filtered, and concentrated. The residue was purified via Biotage (SNAP Cartridge KP Sil 25 g, 0-10% EtOAc/Hexane) to yield 5-bromo-N-[2-(methyloxy)ethyl]-2-nitroaniline (0.374 g, 1.286 mmol, 96 % yield). 1H NMR (400 MHz, CDCI3) delta 8.22 (br. s., 1 H), 8.04 (d, J = 9.1 Hz, 1 H), 7.05 (d, J = 1.5 Hz, 1 H), 6.78 (dd, 1 H), 3.69 (t, 2 H), 3.48 (t, 2 H), 3.45 (s, 3 H); MS (m/z) 275.1 (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; GLAXO GROUP LIMITED; BODMER, Vera, Q.; CASILLAS, Linda, N.; DEMARTINO, Michael, P.; KING, Bryan, W.; LAKDAWALA SHAH, Ami; LEISTER, Lara, Kathryn; WANG, Gren, Z.; WISNOSKI, David, Duff; HARRIS, Philip, A.; RAMANJULU, Joshi, M.; ROMANO, Joseph, J.; WILSON, Matthew, A.; WO2011/123609; (2011); A1;,
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Related Products of 59557-91-4, A common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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: To a solution of 4-bromo-2-methoxyaniline (11a) (300 mg, 1.48 mmol) in anhydrous CH2Cl2(15 mL) was added pyridine (0.24 mL, 2.97 mmol) and 1-propanesulfonyl chloride (0.18 mL, 1.63 mmol) under an argon atmosphere.The mixture was stirred at room temperature for 16 h.After being quenched with 1 N HCl(aq) (1.0 mL), water and CH2Cl2were added and then the layers were separated. The combinedorganic phases were washed with brine, dried over anhydrousNa2SO4, filtered and concentrated. The residue was purified bycolumn chromatography on silica gel (EtOAc/hexane, 10:90 to15:85) to give 13a (490.1 mg, 99%) as a light yellow 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:
Article; Bufton, Joshua C.; Bullock, Alex N.; Cuny, Gregory D.; Dai, Bing; Degterev, Alexei; Duddupudi, Anantha Lakshmi; Gyrd-Hansen, Mads; Hu, Ming; Li, Li; Pinkas, Daniel M.; Schlicher, Lisa; Suebsuwong, Chalada; European Journal of Medicinal Chemistry; vol. 200; (2020);,
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