Tag: M.W=200-300

Reference of 215800-25-2,Some common heterocyclic compound, 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile, molecular formula is C9H8BrN, 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 d intermediate 472-(4-bromo-3-methylphenyl)-2-methylpropanenitrileTo a stirred solution of 2-(4-bromo-3-methylphenyl)acetonitrile (11.2 g, 53.3 mmol) in anhydrous DMF (125 mL) is added methyl iodide (13.2 mL, 213 mmol). The solution is cooled to O0C and sodium hydride (60% susp. in oil, 3.84 g, 160 mmol) is added in small portions over 20 min. The reaction mixture is then left stirring and slowly warmed up to room temperature for 18 h. At O0C, water (500 mL) is then slowly added then extracted with ethyl acetate containing 10% of hexanes. The organic layer is separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-3-methylphenyl)-2- methylpropanenitrile (12.6 g, 99 %) as a clear yellow oil which is used in the next step without further purification. IH NMR (400 MHz, CHLOROFORM-D) 5 ppm 1.71 (s, 6 H) 2.43 (s, 3 H) 7.14 (dd, /=8.40, 2.34 Hz, 1 H) 7.34 (d, /=2.54 Hz, 1 H) 7.53 (d, /=8.40 Hz, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromo-3-methylphenyl)acetonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
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Electric Literature of 51632-29-2,Some common heterocyclic compound, 51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, molecular formula is C14H11NO, 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 1 284 g of 3-phenoxy benzyl cyanide and 220 g of di-ethyl oxalate were mixed and 400 ml of absolute ethanol was added. To this mixture was added gradually a solution of sodium ethoxide (prepared by dissolving 31 g of sodium in 410 ml of absolute ethanol). After the addition of the ethanol solution the mixture was warmed to 50 C for 30 minutes and then allowed to stand at room temperature for 12 hours. The reaction mixture was then acidified with ice-cooled 10% sulphuric acid (prepared by adding 37 ml of concentrated sulphuric acid to sufficient ice to give 370 ml of ice-cooled diluted acid). The product was extracted with methylene dichloride and the methylene dichloride solution was then washed neutral with distilled water. The product was dried over anhydrous sodium sulphate and the solvent removed. This product was treated with cold hexane to give ethyl 3-cyano-3-(3-phenoxyphenyl)-2-ketopropionate, melting point: 105-109, 90%. The structure was confirmed with proton magnetic resonance analysis (purity > 95%). The preparation of the cyanide from the bromide is illustrated in the following example.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Phenoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; Shell Oil Company; US4010190; (1977); 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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17216-62-5

(a) Diethyl 2-(2-cyanoethyl)-2-(5-nitropyrid-2-yl)malonate Sodium hydride (53% dispersion in oil) (30.71 g, 0.66 mole) was washed by decantation with xylene (2*150 ml), ether (150 ml), tetrahydrofuran (THF) (150 ml) and finally suspended in THF (245 ml). Diethyl 2-(2-cyanoethyl) malonate (156 g, 0.73 mole) in THF (80 ml) was added dropwise over 1 hr keeping the internal temperature at 18 C. to 22 C. (with ice bath cooling). The resulting suspension cleared over 15 minutes when 2-chloro-5-nitropyridine (88.3 g, 0.55 mole) was added to give a deep magenta solution. The resulting solution was refluxed for 1 hr and the solvent was removed on the rotary evaporator. The resulting oil was partitioned between water (500 ml) and chloroform (800 ml), the pH was adjusted to ~7 (concentrated hydrochloric acid), and the chloroform was run off. The aqueous layer was extracted with a further (2*250 ml) chloroform, the extracts were combined, dried over magnesium sulphate and the solvent was removed to give an amber oil (~245 g). Ether (150 ml) was added and the solution was allowed to crystallise to give the title compound (121.98 g, 65%), m.p. 59.5-61 C. (Found C, 53.7; H. 5.05; N, 12.35%. C15 H17 N3 O6 requires C, 53.75; H, 5.1; N, 12.55%) NMR (CDCl3, 60 MHz); delta 1.37 (6 H, t); 2.65 (4 H, m); 4.26 (4 H, q); 7.84 (1 H, dd); 8.49 (1 H, dd); 9.32 (1 H, dd).

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 17216-62-5.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4902698; (1990); 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-3,5-dimethylbenzonitrile

Under a nitrogen atmosphere, Add the previous step in a 250 ml three-neck round bottom reaction bottle. 10-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine, 420 mg of 4-bromo-3,5-dimethylbenzonitrile, 120 ml of toluene, 40 ml of absolute ethanol and 40 ml of a 2 molar solution of potassium carbonate per liter, Stir and dissolve. After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming. The reaction system was extracted with a dichloromethane solvent. It was washed three times with deionized water, three times with saturated brine, and dried over anhydrous magnesium sulfate for 1 hour. Purification of the product by column chromatography, The eluent is a mixed solvent of petroleum ether and dichloromethane in a ratio of 3:1. The yield of the solid product was finally 77%.

According to the analysis of related databases, 75344-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C9H8BrN

To a solution of 4-bromo-3,5-dimethylbenzonitrile (1 g) in N,N-dimethylformamide (10 ml_) is added NH4CI (770 mg) and NaN3 (800 mg) and the mixture is heated to 100C for 12 hours. After cooling to room temperature the mixture is diluted with water. The formed precipitate is filtered off, washed with water and dried to give the title compound. Yield: 650 mg; Mass spectrum (ESI+): m/z = 253 [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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (2013); A1;,
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Synthetic Route of 1835-65-0,Some common heterocyclic compound, 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, molecular formula is C8F4N2, 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.

One hundred (100) g of the benzonitrile solution as the mother liquor obtained in Example 8 and 80 g of an aqueous 70percent sulfuric acid solution added thereto were stirred together at room temperature for 2 hours. Then, the resultant reaction solution was left standing at rest and allowed to separate into an organic layer (benzonitrile solution layer) and a water layer. When the organic layer was analyzed, it was found to contain absolutely no benzoic acid fluoride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5,6-Tetrafluorophthalonitrile, its application will become more common.

Reference:
Patent; Nippon Shokubai Co., Ltd.; US6392084; (2002); B1;,
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Synthetic Route of 58633-04-8, 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 58633-04-8 as follows.

EXAMPLE 2 Preparation of 3,5-Dibromobenzonitrile STR16 To a stirred solution of t-butylnitrite (53.5 muL, 0.449 mmoles) in 1 ml sieve dried dimethylformamide at 50 C. under an atmosphere of nitrogen was added a solution of 4-amino-3,5-dibromobenzonitrile (50 mg, 0.179 mmoles) in 1 mL of DMF. The mixture was stirred at 50 C. for 0.5 hour and partitioned between diethyl ether, ice-water, and ammonium chloride. The organic phase was separated, washed with water and brine, dried over anhydrous sodium, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (9:1) as eluant provided 28 mg (59%) of white, crystalline product. NMR(CDCl3) delta: 7.7 (d, J=1.8Hz, 2H), 7.9 (t, J=1.8Hz, 1H).

According to the analysis of related databases, 58633-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US5192758; (1993); A;,
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Application of 114897-91-5, 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 114897-91-5 as follows.

Step (2) Preparation of N’-Hydroxy-2-(4-bromo-2-fluorophenyl)ethanimidamide Hydroxylamine hydrochloride (8.93 g, 128.5 mmol), was added in one portion to a solution of sodium methoxide, freshly prepared from sodium (2.96 g, 128.5 mmol) in methanol (200 mL). The resulting mixture was stirred 1 hour at room temperature, during which a precipitate was formed. 4-Bromo-2-fluorophenylacetonitrile (11.0 g, 51.4 mmol) was added and the resulting mixture heated to reflux for 20 hours. A white solid was removed by filtration of the hot mixture and discarded. The filtrate was concentrated to a volume of 100 mL to give a precipitate which was washed with water, followed by 5% EtOAc/hexanes. A second crop was obtained from the filtrate upon further concentration. The two crops were combined and dried in vacuo to give the product as a white crystalline solid (10.4 g, 82%) of sufficient purity for use in the subsequent reaction. NMR (DMSO-d6): delta 8.99 (s, 1H), 7.44 (dd, J1 =9.2 Hz, J2 =1.3 Hz, 1H), 7.32 (m, 2H), 5.47 (br s, 2H), 3.30 (s, 2H).

According to the analysis of related databases, 114897-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corp.; US4895862; (1990); A;,
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These common heterocyclic compound, 1835-49-0, name is Tetrafluoroterephthalonitrile, 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. Product Details of 1835-49-0

[Example 7]; The same operations as in Example 1 were carried out, except that the catalyst used was changed from the 5% Rh/C catalyst (available from NE Chemcat Corporation, hydrous product) to a 2% Rh/C catalyst (available from NE Chemcat EPO Corporation, hydrous product) . After a lapse of 7.3 hours, absorption of hydrogen ceased. The quantity of hydrogen absorbed was 114% of the theoretical quantity of hydrogen absorbed. Treatment of the reaction solution was carried out in the same manner as in Example 1.From the toluene extract, a small amount of a sample was withdrawn, and it was subjected to GC analysis. As a result of the analysis, a peak of the tetrafluoroterephthalonitrile as a raw material was below the detection limit, the amount of tetrafluoroterephthalaldehyde was 88.6 mol%, the amount of 2, 3, 5, 6-tetrafluorobenzene was 1.15 mol%, and the amount of 2, 3, 5, 6-tetrafluorobenzonitrile was 2.63 ralphaol%. On the other hand, the aqueous phase was neutralized and then subjected to GC analysis. As a result of the analysis, presence of 2.36 mol% of 2, 3, 5, 6-tetrafluorobenzylamine was confirmed. The results are set forth in Table 1.

The synthetic route of Tetrafluoroterephthalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHOWA DENKO K.K.; WO2006/137347; (2006); A2;,
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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. 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-5-trifluoromethylbenzonitrile

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C. for 21/2 hours. The reaction mixture is cooled and poured into de-ionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

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; Rohm and Haas Company; US4419122; (1983); A;,
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