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. 92616-49-4, name is 4-Bromo-1-naphthonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 92616-49-4

19.5g (84mmol) 4-bromo-1-naphthonitrile, 5.88g (48mmol) hydroxylamine hydrochloride, 4.65g (84mmol) sodium methoxide in a methanol solvent paste has better mouth feeling and the reflux time 18. Reactants as ethyl acetate 10% sodium hydroxide aqueous solution 3 which has ethyl water insoluble chemical additives present after extracted times. Saline to which washes the 3 times during the drying process and magnesium sulfate anhydride, filtration, after concentrating dissolved back to solvent ethanol 16 doesn’t have any error frames, Raney nickel 2g the reflux time. Product to filter out removing the catalyst after concentrated within, silica gel chromatography (CHCl2/ethanol) purified after solid compound (10.0g) of 48% are obtained

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; Choe, Don Soo; Jo, Yun Hwan; (92 pag.)KR2015/80966; (2015); 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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-3-fluorophenylacetonitrile

A solution of 2-(4-bromo-3-fluorophenyl)acetonitrile (0.78 g, 3.64 mmol) in H2SO4 (5 mL) and H20 (5 mL) was stirred at 100 C for 16 h. After LCMS analysis showed the starting material had disappeared, the mixture was dissolved in H20 (20 mL) and extracted by EA (20 mL). The organic layer was dried over Na2S04, filtered and concentrated to yield a white solid of 2-(4- bromo-3-fluorophenyl)acetic acid (0.7 g, 2.046 mmol, 56.1% yield): l NMR (400 MHz, CD3OD) 5 7.53 (t, J= 7.8 Hz, 1H), 7.16 (dd, J =9.8, 1.9 Hz, 1H), 7.02 (d, J= 8.0 Hz, 1H), 3.61 (s, 2H).

The synthetic route of 499983-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; EIDAM, Hilary Schenck; DEMARTINO, Michael P.; GONG, Zhen; GUAN, Amy Huiping; RAHA, Kaushik; WU, Chengde; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; CHEUNG, Mui; WO2014/141187; (2014); A1;,
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Electric Literature of 99066-80-5, 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. 99066-80-5 name is Methyl 3-cyano-5-nitrobenzoate, 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.

10%Pd/C (0.9 g) was added to the solution of methyl-3-cyano-5-nitrobenoate (25 mmol) in MeOH (200 mL) and THF (100 mL). Then the solution was stirred at room temperature for 4 hours. After filtration, it was concentrated to give methyl-3-amine-5-cyanobenoate in 95% yield.

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

Reference:
Patent; Hutchison Medipharma Enterprises Limited; US2009/118292; (2009); A1;,
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Synthetic Route of 114897-91-5,Some common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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: 2- (4-BROMO-2-CHLORO-PHENYL)-2-METHYL-PROPIONITRILE (4-BROMO-2-FLUOROPHENYL) ACETONITRILE (1 g, 4.67 mmol) described in step 1 from Example A (97), benzyltriethylammonium chloride (0.02 g, 0.09 mmol) and 1,4-Dibromobutane (1.43 g, 0.79 mmol) were dissolved 50% aqueous NAOH (3 mL) and the resulting mixture was stirred for 3 hours at 50 C. Reaction was quenched with 4N HCI (50 mL extracted with EtOAc. The organic phase was dried over NA2SO4 and evaporated. The crude organic product was purified by flash column chromatography (5% EtOAc in hexanes) to give the product (1.25 g, 100%) as a clear OIL). H NMR (CDCI3) 5 : 1. 93-2. 17 (m, 4 H), 2.50-2. 55 (m, 2 H), 3.42-3. 46 (m, 2H), 7.26-7. 34 (m, 3 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-2-fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
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Reference of 1953-99-7, These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

100 mL flask Of Synthesis Example 1-2 4- (2-tert-Butyl-4-methoxy-phenoxy) -3,5,6-trichloro-phthalonitrile (1.1 g) 3,4,5,6-Tetrachlorophthalonitrile (0.71 g), 1,8-Diazabicycloundec-7-ene (1.02 g) And 1-pentanol (14 g) were added, and the mixture was heated at 90 ¡ã C to dissolve the solid. Then, zinc acetate (0.25 g) was added thereto and stirred while heating to 140 ¡ã C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried under vacuum to obtain a compound represented by the following general formula (10).

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Shin Myeong-yeop; Seo Hye-won; Jeong Ui-su; Han Gyu-seok; (41 pag.)KR2019/27185; (2019); A;,
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Application of 13338-63-1,Some common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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 Preparation of (Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 3.0 g of 3-nitro-4-methoxybenzaldehyde, 3.4 g of 3,4,5-trimethoxyphenylacetonitrile, 800 mg of sodium hydroxide and 100 mg of octylmethylammonium chloride were dissolved in 15 ml of water and 15 ml of dichloromethane and reacted for 4 hours at room temperature. Ice water was added to the reaction liquid, which was then extracted three times each with dichloromethane. The extract was dried with anhydrous sodium sulfate and concentrated. The concentrated liquid was purified by crystallization (ethyl acetate) to obtain 4.4 g of the intended compound. The yield was 72%. 1 H-NMR(CDCl3): 8.30 (1H, dd, J=2.4, J=9.0), 8.21 (1H, d, J=2.4), 7.38 (1H, s), 7.21 (1H, d, J=9.0), 6.86 (2H, s), 4.05 (3H, s), 3.94 (6H, s), 3.89 (3H, s); mass spectrum (m/z): 370 (M+); melting point 191-192 C.

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-Trimethoxyphenylacetonitrile, its application will become more common.

Reference:
Patent; Ajinomoto Co., Ltd.; US5525632; (1996); 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 1000577-76-3 as follows. Computed Properties of C7H2BrClFN

Intermediate 573-Chloro-2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile; is A suspension of 5-bromo-3-chloro-2-fluorobenzonitrile (0.959 g, 4.09 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (2.08 g, 8.18 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) chloride (0.234 g, 0.29 mmol), and potassium acetate (1.20 g, 12.3 mmol) in dioxane (15 mL), was placed in a microwave vial. The mixture was degassed with a stream of argon for a couple of min, and the reaction mixture was then heated to 110 C. for 1 h in a microwave reactor. The reaction mixture was cooled to r.t., filtered through diatomaceous earth, and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography using heptane/EtOAc (70/30) as eluent to give the title compound (1.22 g, quantitative yield): GC MS (EI) m/z 282 M+.

According to the analysis of related databases, 1000577-76-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
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Electric Literature of 858523-37-2, 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. 858523-37-2 name is (4-Bromo-2-methoxyphenyl)acetonitrile, 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.

Preparation 6(S)-3-(4-Bromo-2-hydroxy-phenyl)-pyrrolidine-l-carboxylic acid tert-bntyl ester The synthetic procedure described in this Preparation was carried out according to the process shown in Scheme G. EPO SCHEME GStep 1 (4-Bromo-2-methoxy-phenyl)-acetic acid; A solution of NaOH (5.72 g, 143 mmol) in water (29 mL) was added to a solution of (4- bromo-2-methoxy-phenyl)-acetonitrile (10.2 g, 45.1 mmol) in MeOH (100 mL). The reaction mixture was heated at reflux for 18 hours. The solvent was evaporated under reduced pressure and water was added. The aqueous mixture was washed with diethyl ether, and the aqueous layer was acidified by addition of aqueous HCl (2 M) to pH 1. The aqueous mixtuer was then extracted with EtOAc, and the combined organic extracts were washed with brine, dried OVCrNa2SO4, filtered, and evaporated under reduced pressure to give 9.49 g (86% yield) of (4-bromo-2-methoxy-phenyl)-acetic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-Bromo-2-methoxyphenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/55847; (2008); A1;,
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Synthetic Route of 90110-98-8, 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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

At 0-10C, anhydrous ethanol (27 mL) was slowly added dropwise into a mixture of selenium powder (2.7 g, 34.2 mmol) and sodium borohydride (1.57 g, 41.5 mmol), then heated to room temperature and stirred for 30 min, and then added with pyridine solution (7.2 mL) containing 3-bromo-4-isopropylthiomethyl benzonitrile (63) (1.8 g, 8.49 mmol). The reaction solution was heated until reflux occurred, slowly added dropwise with 2M hydrochloric acid solution (18 mL) and then stirred under reflux for 1 h. A TLC analysis indicated that the reaction was completed. The solution was cooled to room temperature, added with a proper amount of water and then extracted with ethyl acetate (30 mL¡Á3). The organic phase was respectively washed with 2M hydrochloric acid (20 mL) and saturated saline solution (20 mL), and dried with anhydrous sodium sulfate. The solvent was removed by means of reduced pressure distillation, so as to obtain pink 3-bromo-4-hydroxymethyl selenobenzamide (64) (1.98 g), with a yield of 79.6%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Atom Bioscience and Pharmaceutical Co. Ltd.; SHI, Dongfang; FU, Changjin; WU, Jie; LIU, Jun; EP2927219; (2015); A1;,
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Electric Literature of 328-87-0, A common heterocyclic compound, 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, molecular formula is C8H3ClF3N, 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.

EXAMPLE I Into 100 ml. of ethanol is added 12.4 g. (0.10 moles) of benzylmercaptan. While nitrogen is bubbled into the solution, 100 ml. of a 1 molar sodium ethoxide in ethanol solution is added. The solvent is evaporated and 100 ml. of anhydrous dimethylformamide is added to the crude solid sodium mercaptide. To the resulting solution is then added 21 g. (0.10 moles) of 4-chloro-3-cyanobenzotrifluoride. The reaction mixture is stirred under nitrogen at room temperature for 1/2 hour and then poured into about 800 ml. of ice-water. After stirring this mixture for 5 minutes, it is extracted with four 200 ml.-portions of ether. The extracts are combined, dried over anhydrous sodium sulfate and evaporated to provide, after drying under high vacuum, a pale yellow oil that crystallizes to a solid upon standing. The yield of crude 2-benzylthio-5-trifluoromethylbenzonitrile is 27.4 g. (94 percent).

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US3954994; (1976); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts