Tag: M.W=200-300

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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 179897-89-3

(1) 5-bromo-2-fluoro-1-cyanobenzene (II, 3 g, 15 mmol) under N2 protection,Sodium sulfide (1.3 g, 16.5 mmol) was reacted in DMF (30 mL) at room temperature for 5 h.Add 300 mL of sodium hydroxide solution (1 mol/L) and stir for 0.5 h.Wash with dichloromethane (300 mL ¡Á 2), acid phase with hydrochloric acid (6 mol / L) to pH = 2, dichloromethane (400 mL ¡Á 2),The combined organic layers were washed with brine, dried over anhydrous magnesium5-bromo-2-thio-1-cyanobenzene (III)1.0 g, yield 31.2%.

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; South China University of Technology; Li Jing; Li Xiaolei; Zhou Haiyan; Wu Fangping; Zhang Lei; (12 pag.)CN108218777; (2018); A;,
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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 916792-13-7 as follows. Safety of 4-Bromo-2-fluoro-5-methylbenzonitrile

4-Bromo-2-fluoro-5-methylbenzamide In a 100-mL round bottom flask, 4-bromo-2-fluoro-5-methylbenzonitrile (5 g, 23.36 mmol, 1.00 equiv) was dissolved in a mixture of sulfuric acid (40 mL) and trifluoroacetic acid (10 mL) at room temperature. The resulting solution was then stirred overnight at 80 C. When the reaction was done, it was diluted with 200 mL water/ice and precipitation happened. The resulting precipitate was collected by filtration, rinsed with water and dried under reduced pressure to afford 4-bromo-2-fluoro-5 methylbenzamide (4.8 g, 89%) as white solid. MS: m/z=232.1 [M+H]+.

According to the analysis of related databases, 916792-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
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Electric Literature of 58633-04-8, 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. 58633-04-8 name is 4-Amino-3,5-dibromobenzonitrile, 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 26 PREPARATION OF 3,5-DIBROMOBENZONITRILE STR38 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 the 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).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3,5-dibromobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co. Inc.; US5455239; (1995); A;,
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Some common heterocyclic compound, 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, molecular formula is C7H3BrClN, 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: C7H3BrClN

To a solution of 2-bromo-4-chlorobenzonitrile (500 mg, 2.3 mmol), in dry THF (50 mL) was added slowly borane-THF complex (1 M, 12 mL, 1 1 .5 mmol) at 0 C before refluxing for 1 h. After cooling down, 1 M HCI in MeOH (20 mL) was charged slowly with ice cooling. The solvent was removed by concentration in vacuo before water (0.61 mmol/mL to benzonitrile) was charged, then washed by Et20 (0.61 mmol/mL to benzonitrile) before basifying with 2 M NaOH solution to pH 12. Et20 (15 mL) was added and the mixture was washed with water (3 x 15 mL) and brine (1 mL). The organic phase was dried (MgS04) and concentrated in vacuo to give a yellow oil (345 mg, 68%). LCMS (EST) m/z = 220.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-49-4, its application will become more common.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; CHESSARI, Gianni; HOWARD, Steven; BUCK, Ildiko Maria; CONS, Benjamin David; JOHNSON, Christopher Norbert; HOLVEY, Rhian Sara; REES, David Charles; ST. DENIS, Jeffrey David; TAMANINI, Emiliano; GOLDING, Bernard Thomas; HARDCASTLE, Ian Robert; CANO, Celine Florence; MILLER, Duncan Charles; CULLY, Sarah; NOBLE, Martin Edward Maentylae; OSBORNE, James Daniel; PEACH, Joanne; LEWIS, Arwel; HIRST, Kim Louise; WHITTAKER, Benjamin Paul; WATSON, David Wyn; MITCHELL, Dale Robert; (293 pag.)WO2017/55860; (2017); 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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromo-2-fluorobenzonitrile

Referential Example 3 5-Bromo-2-fluorobenzonitrile and piperidine were heated at 80C in DMSO in the presence of cesium carbonate to obtain 5-bromo-2-piperidin-1-ylbenzonitrile. F: 265.

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 179897-89-3.

Reference:
Patent; Astellas Pharma Inc.; EP1783116; (2007); A1;,
Nitrile – Wikipedia,
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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 950596-58-4 as follows. SDS of cas: 950596-58-4

Example 3: Preparation of Erlotinib Trifluoro acetate2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile (25 g) was charged into ethanol (350 ml) at 25C to 300C and stirred for 10 minutes to 15 minutes to get a clear solution. 3-ethynyl aniline (11.1 g) followed triethyl orthoformate (20.86g) was charged into reaction mass at 25C to 300C. Trifluoroacetic acid (3.8ml) was added slowly drop-wise into the reaction mixture at 250C to 300C and stirred for 30 minutes at 25C to 300C. Trifluoroacetic acid (3.8ml) was added slowly drop wise to reaction mixture at 250C to 300C and stirred for 30 minutes at 25C to 300C. Again, trifluoroacetic acid (3.8ml) was added slowly drop wise to reaction mixture at 250C to 300C and stirred for 30 minutes at 250C to 300C. The reaction mixture was refluxed for about 24 hours at 750C to 800C and Cooled to 25C to 300C. Ethanol (-150 ml) was recovered from the reaction mixture under vacuum at 55C to 600C. The solution obtained was Cooled to 25C to 300C and stirred for about 18 hours at 25C to 300C. The solid obtained was filtered, washed with ethanol (2x25ml) and dried under vacuum for about 18 hours at 400C to 450C to give erlotinib trifluoroacetate.Yield: 29.2 g. Purity: 97.35%

According to the analysis of related databases, 950596-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; MURUGESAN, Balaguru; VEMPALI, Anandam; SATHYANARAYANA, Swargam; THAPER, Rajesh, Kumar; PRASAD, Mohan; WO2010/109443; (2010); A1;,
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Application of 1953-99-7,Some common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-isopropylphenol (2.5608 g), K2CO3 (3.898 g), and N,N-dimethylformamide (50 ml) are put in a 100 ml flask and then stirred while heated at 50¡ã C. When a reaction is complete, an extraction is performed with EA (ethyl acetate). After the extraction, a liquid column-purified through column chromatography with EA/hexane is concentrated to obtain a solid, and the solid is vacuum-dried, obtaining a compound according to Synthesis Example 6.

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-Tetrachlorobenzene-1,2-dicarbonitrile, its application will become more common.

Reference:
Patent; Samsung SDI Co., Ltd.; PAK, Chae Won; SEO, Hye Won; SHIN, Myoung Youp; JEONG, Eui Soo; CHOI, Seung Jib; (35 pag.)US2017/107224; (2017); A1;,
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Related Products of 13544-06-4,Some common heterocyclic compound, 13544-06-4, name is 2-(2-Nitro-4-(trifluoromethyl)phenyl)acetonitrile, molecular formula is C9H5F3N2O2, 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.

1.75 g (7.6 mmol) (2-Nitro-4-trifluoromethylphenyl)-acetonitrile in 20 ml THF are cooled to 0C in a nitrogen atmosphere and treated with 60 mi BH3/THF- complex (1 M in THF). The reaction mixture is allowed to slowly warm up to room temperature overnight. After 72 h the reaction solution is slowly given to 50 ml 5 N HO gegeben and then 1 h heated to reflux. The reaction mixture is evaporated to dryness, the residue made alkaline (pH 12-14) with 25% NaOH solution and extracted 2x with 100 mi ethylacetate. The combined organic phases are washed with brine, dried using Na2SO4, filtered and evaporated. Yield : 1.8 g (77 %) 112, brown oil

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

Reference:
Patent; MERCK PATENT GMBH; WO2005/75425; (2005); A2;,
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Related Products of 330792-69-3, These common heterocyclic compound, 330792-69-3, name is 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile, 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.

1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene (22.5 g) and 1,1-dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene oil (15 g) are treated with a solution of hydrazine hydrate (18 mL) in ethanol (25 mL) and heated on the steambath for 1 hour. Ethanol (15 mL) is added followed by water (10 mL). The precipitated solid is collected and washed with ethanol:water (4:1) and then dried in air to give 3-amino-4-cyano-5-(4-phenoxyphenyl)pyrazole as a pale orange solid.

Statistics shows that 2-(Methoxy(4-phenoxyphenyl)methylene)malononitrile is playing an increasingly important role. we look forward to future research findings about 330792-69-3.

Reference:
Patent; Pharmacyclics, Inc.; US7718662; (2010); B1;,
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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. 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-4-fluorobenzonitrile

Method 10B: the bromophenol was prepared using the appropriate fluorobromobenzene with methanesulfonylethanol.Under inert atmosphere, to a solution of the fluorinated derivative in dimethylformamide was added methylsulfonylethanol (1.5eq). The mixture was stirred at 0 C. before adding sodium hydride (5eq). The reaction mixture was stirred at room temperature, then acidified with 1M hydrochloric acid solution to pH 2, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed over silica gel.Example 10.4. 2-bromo-4-hydroxybenzonitrile Prepared following the method previously described (Method 10B) using 2-bromo-4-fluorobenzonitrile. The product was chromatographed over silica gel (elution gradient petroleum ether/ethyl acetate 90/10 to 80/20). The product was obtained as a white solid. Yield: 95% Rf (petroleum ether/ethyl acetate 70/30): 0.25 NMR 1H (CDCl3): 5.95 (s, 1H); 6.87 (dd, 1H, J=8.5 Hz, J=2.4 Hz); 7.17 (d, 1H, J=2.4 Hz); 7.54 (d, 1H, J=8.5 Hz).

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; GENFIT; US2010/4159; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts