Month: May 2021

874285-03-7, name is 3-Bromo-2-fluorophenylacetonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-Bromo-2-fluorophenylacetonitrile

1.17 g of (3-bromo-2-fluorophenyl)acetonitrile and 15 mLof anhydrous DMSO were placed under nitrogen in an oven-dried flask. 459 mg of sodium hydride (60% dispersion in oil) were added, and the mixture was stirred at room temperature for 1 hour. 0.86 g of 2-chloroethyl ether dissolved with 2 ml anhydrous DMSO was added, and the mixture was stirred at room temperature overnight. 0.65 ml_ of glacial acetic acid was added, and the reaction was diluted into ethyl acetate, extracted with water and 5% sodium chloride, dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography on silica. The product fractions were concentrated and vacuum dried to give 730 mg of product. GCMS (M) 283; 1 H NMR (400 MHz, DMSO-c/6) delta ppm 2.04 – 2.15 (m, 2 H) 2.17 – 2.25 (m, 2 H) 3.69 (td, J=12.08, 1.88 Hz, 2 H) 4.01 (dd, J=11.95, 2.82 Hz, 2 H) 7.27 (td, J=7.92, 1.07 Hz, 1 H) 7.47 – 7.55 (m, 1 H) 7.80 (ddd, J=8.12, 6.65, 1.61 Hz, 1 H).

The synthetic route of 874285-03-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; WO2009/69044; (2009); A1;,
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Synthetic Route of 64113-86-6, The chemical industry reduces the impact on the environment during synthesis 64113-86-6, name is 5-Methyl-2-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

A reaction product as prepared in Step 2 (84 g, 0.52 mol) was added to a solution of 4-methoxycarbonylbenzaldehyde (77.4 g, 0.47 mol) in tetrahydrofuran, and the mixture was stirred for 30 minutes at ambient temperature. 1,1,3,3-tetramethylguanidine (60.8 mL, 0.48 mol) was dissolved in THF (600 mL) and charged. The resulting mixture was stirred with heating at reflux for 4.5 days. The reaction was cooled to 25 C., and a mixture of AcOH (84 mL) and water (600 mL) was added drop-wise while stirring. The precipitate was filtered off and mixed with acetone (500 mL). the resulting solid was filtered off, washed with acetone, and dried to yield a yellow solid product (77.1 g, 53% yield). The overall reaction is shown below.

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, 5-Methyl-2-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chelsea Therapeutics, Inc.; US2009/253719; (2009); 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. 175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 175596-01-7

A mixture of methyl 4-cyano-2-fluorobenzoate (2) (1 .0 g, 5.6 mmol) and 50% (0607) aq. hydroxylamine (6.84 mL, 1 12 mmol) in EtOH (30 mL) was stirred at reflux for 18 h. The reaction mixture was cooled to RT, diluted with H20 (20 mL) and extracted with EtOAc (60 mL). The organic solution was washed with brine (100 mL), dried over MgS04, filtered and concentrated in vacuo to give methyl 2-fluoro-4-(//’- hydroxycarbamimidoyl) benzoate (3) (260 mg, 22%) as a 1 :1 mixture of methyl and ethyl esters that was progressed without purification: m/z 227, 213 [M+H]+ (ES+)

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; BORTHWICK, Alan David; MILLS, Mark Trevor; BROWN, Jane Theresa; CORCORAN, Jonathan Patrick Thomas; DE CASTRO VASCONCELOS GONCALVES, Maria Beatriz; KALINDJIAN, Sarkis Barret; (161 pag.)WO2016/97004; (2016); A1;,
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57775-06-1, name is 2-(2-Bromophenyl)-2-methylpropanenitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 2-(2-Bromophenyl)-2-methylpropanenitrile

To a solution of 2-(2- bromophenyl)-2-methylpropanenitrile (4.0 g, 17.8 mmol), in dry THF (40 mL) was added borane-dimethyl sulfide (5.08 mL, 53.5 mmol) at 0 °C and the reaction mixture was slowly brought to rt, stirred for 1 h and then, heated to reflux for 18 h. The solvent was removed and quenched with MeOH, and heated to reflux for 18 h. The reaction was concentrated and the residue was dissolved in EtOAc, washed with H2O, brine, dried (Na2SO4), flltered and concentrated to give 4.0 g of 103 A as a white solid. MS (ESI) m/z: 230.2 (M+H)+.

The synthetic route of 57775-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56034; (2013); A1;,
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Electric Literature of 133541-45-4, 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. 133541-45-4 name is 4-Bromo-2,5-difluorobenzonitrile, 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.

To a stirred suspension of 4-bromo-2,5-difluorobenzonitrile (91 g, 417 mmol) and potassium carbonate (173g, 1.25 mol) in N,N-dimethylformamide (910 ml) was added (S)-1,1,1-trifluoropropanol [CAS 3539-97-7] dropwise (52.4g, 460 mmol). The resulting mixture was heated at 70 C for for 15 hours and cooled to room temperature. The reactionwas concentrated and the residue was diluted with water. The aqueous solution was extracted with DCM (3x). Thecombined organic washes were washed with brine, dried over sodium sulfate, filtered, and concentrated under reducedpressure to give an oil (136.6 g). The residue was triturated with a mixture of hexanes and toluene (9:1, 200 mL) to givethe desired product as a white solid (90.3 g, 93% purity, 64% yield).LC-MS (Method A): Rt = 1.29 min; MS (ESIpos): m/z = 312.0 [M+H]+.1H-NMR (400 MHz, CHLOROFORM-d) delta [ppm]: 1.511 (4.41), 1.531 (15.64), 1.533 (16.00), 1.548 (15.84), 1.550 (15.83),4.566 (1.08), 4.581 (2.68), 4.597 (3.18), 4.612 (2.62), 4.626 (1.01), 7.194 (5.27), 7.207 (7.60), 7.220 (7.57).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Bayer AG; Gradl, Stefan, Nikolaus; Niehues, Michael; Halfbrodt, Wolfgang; (43 pag.)EP3553052; (2019); A1;,
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Related Products of 140860-51-1, 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 140860-51-1 as follows.

To a soln. of 2-bromo-4-methoxybenzonitrile (1 g,4.72 mmol )in MeCN (40 rnL) was added Nal (212 g, 14.15 mrnol ) and TMSC1 (1.54 g, 14.15 mmoi). Then the mixture was stirred at 80C overnight, Then the mixture was concentrated in. vacuo and poured into water basified with Na2CO3. The mixture was extracted with EtOAc. The aq. layer was acidified with HC1 and extracted with EtOAc. The organic layer was washed withbrine, dried (Na2SO4). and concentrated in vacuo to give the title compound.

According to the analysis of related databases, 140860-51-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ADAMS, Gregory, L.; COX, Jason, M.; DEBENHAM, John, S.; EDMONDSON, Scott; GILBERT, Eric, J.; GUO, Yan; JIANG, Yu; JOSIEN, Hubert; KIM, Hyunjin, M.; LAN, Ping; MIAO, Shouwu; PLUMMER, Christopher, W.; RAJAGOPALAN, Murali; SHAH, Unmesh; SUN, Zhongxiang; TRUONG, Quang, T.; UJJAINWALLA, Feroze; VELAZQUEZ, Francisco; VENKATRAMAN, Srikanth; SUZUKI, Takao; WANG, Nengxue; (182 pag.)WO2017/205193; (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. 133550-33-1, name is 2-Cyano-N-(3-phenylpropyl)acetamide, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C12H14N2O

General procedure: To a stirred solution of N-alkyl-substituted 2-cyanoacetamide 1 (5mmol) in toluene (10 mL) was added NaN3 (3 equiv) and triethylamine hydrochloride salt (3 equiv). The reaction mixture was heated to 90 C for 20 h. Ice-cold H2O (25 mL) was added to the reaction mixture and acidified with aq HCl and stirred at 0 C for 30 min. The precipitated product was collected by filtration, washed with cold H2O(25 mL), and dried in vacuum (Table 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 133550-33-1.

Reference:
Article; Wang, Yuanze; Patil, Pravin; Doemling, Alexander; Synthesis; vol. 48; 21; (2016); p. 3701 – 3712;,
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These common heterocyclic compound, 109305-98-8, name is 2-Bromo-4,5-dimethoxybenzonitrile, 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. COA of Formula: C9H8BrNO2

General procedure: S3 (1.5 mmol) was dissolved in NEt3 (5 mL) and degassed for 30 minutes at room temperature. Then PdCl2(PPh3)2 (0.2 mol%), CuI (0.2 mol%) and the alkyne were added to S3/NEt3 solution. The obtained dark brown suspension was stirred for 12 h at 60C. After cooling to room temperature the solvent of the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1t-1w (in 76-83% yield).

The synthetic route of 2-Bromo-4,5-dimethoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
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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. 19295-57-9, name is 3-Hydroxy-2,2-dimethylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 19295-57-9

To a solution of 3-hydroxy-2,2-dimethylpropanenitrile (0.5 g) in dichloromethane (8 ml_) and pyridine (1 .5 ml_) is added at 0C p-toluene-sulfonylchloride (1 .0 g) in portions. The mixture is stirred for 12 hours at room temperature, diluted with diethylether and washed with 1 M aqueous HCI solution and brine. After drying (MgSO4) the solvent is evaporated and the residue is chromatographed on silica gel (petrole ether/ethyl acetate 90:10?50:50) to give the title compound. Yield: 770 mg; Mass spectrum (ESI+): m/z = 254 [M+H]+.

According to the analysis of related databases, 19295-57-9, the application of this compound in the production field has become more and more popular.

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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Related Products of 51632-12-3, 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 51632-12-3 as follows.

1-1 (21.3 g, 89.6 mmol) is dissolved in DMF (300 mL). The mixture is cooled to 0 C and NaH (60% in oil suspension, 3.76 g, 94.1 mmol) is added slowly. The mixture is then stirred for a further 15 minutes and methyl iodide (5.9 mL, 94.1 mmol) is added. The reaction mixture is stirred at 0 C to room temperature for 2 hours and then concentrated in vacuo. The residue is partitioned between methylene chloride and brine. The combined organics are dried with Na2S04, filtered and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-15% EtOAc in hepatne) to give the title intermediate (21.7 g); m/z 252.3, 254.3 [M/M+2H].

According to the analysis of related databases, 51632-12-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BARTOLOZZI, Alessandra; BOSANAC, Todd; CHEN, Zhidong; DE LOMBAERT, Stephane; HUBER, John; LO, Ho Yin; LOKE, Pui Leng; LIU, Weimin; MORWICK, Tina Marie; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee; WO2012/24150; (2012); A1;,
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