Month: November 2020

403-54-3, 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. 403-54-3, name is 3-Fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 3-methylbenzonitrile (5 mmol), benzyl acetate (6mmol), and Fe(ClO4)3¡¤H2O (5 mol%) was placed in a round-bottomedflask. Then, the reaction mixture was heated at 80 C for5 h. After completion of the reaction monitored by thin layerchromatography (TLC), water (10 mL) was added, and the reactionmixture was extracted with ethyl acetate (3 ¡Á 20 mL). Theorganic layers were collected, combined, washed with water (3¡Á 20 mL), dried with anhydrous Na2SO4, and concentrated undervacuum. The pure product was obtained by directly passingthrough a silica gel (200-300 mesh) column to give a whitepowder n (0.96 g, 86% yield)..

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
Nitrile – Wikipedia,
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326-62-5, These common heterocyclic compound, 326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, 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.

2-(2-fluorophenyl)acetonitrile (3.000 g, 22.199 mmol) and sodium hydride (60.00%, 1.953 g, 48.838 mmol) in N,N-dimethylformamide (150 mL) at 0 C to this mixture 1,3-dibromopropane (2.253 mL, 22.199 mmol) was added and stirred at 50 C for 17 hours, the temperature was lowered to room temperature, saturated sodium bicarbonate aqueous solution (10 mL) was added to the reaction mixture at 0 C, and the reaction was terminated by stirring for 10 minutes. The solvent was removed from the reaction mixture under reduced pressure, the obtained concentrate was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate/hexane = 0% to 10%) and concentrated to give the title compound (2.000 g, 51.4%) as a colorless oil.

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 326-62-5.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Nitrile – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, I believe this compound will play a more active role in future production and life. 170572-49-3

Preparation C; 4-(Bromomethyl)-3-fluorobenzonitrile; Method A. NBS/AIBN Bromination; 1,2-Dichloroethane (151 kg) was charged to a suitable vessel along with 4-cyano-2-fluorotoluene (24 kg) and AIBN (2 kg). The mixture was heated to 7074 C. Once the batch temperature reached 70 C., N-bromosuccinimide (47.4 kg) was added in portions at the rate of 12 kg/h, maintaining the temperature at 7074 C. (it is important to control addition rate to avoid exothermic reaction). The mixture was sampled via GC detection after 24 kg of N-bromosuccinimide was added, and the reaction was heated at 70-74 C. until complete reaction was observed. The mixture was cooled to 0-5 C. and allowed to stand for 2 additional hours. The mixture was filtered, and the cake was washed with MTBE (24 kg). The filtrate was washed with water (3¡Á65 kg). The organic layer was dried with sodium sulfate (10.3 kg) for 6 hours, filtered and the cake was washed with MTBE (24 kg). The solution was evaporated under reduced pressure, ethanol (12 kg) was added and the mixture was heated to 40-45 C., then cooled slowly to 0-5 C. while stirring to crystallize. The mixture was filtered and the cake was washed with cold ethanol (5 kg). The crude solid was recrystallized from petroleum ether, filtered and washed with petroleum ether (10 kg), giving the title compound 4-(bromomethyl)-3-fluorobenzonitrile as an off white solid (21 kg, 55% yield). 1H NMR (300 MHz, CDCl3) delta ppm 4.46-4.50 (m, 2 H) 7.36 (dd, J=8.85, 1.32 Hz, 1H) 7.44 (dd, J=7.91, 1.32 Hz, 1H) 7.52 (dd, J=7.91, 7.16 Hz, 1 H). 13C NMR (75 MHz, CDCl3) delta ppm 23.65 (d, J=4.60 Hz, 1C) 113.76 (d, J=9.77 Hz, 1C) 117.09 (d, J=2.87 Hz, 1C) 119.44 (d, J=24.71 Hz, 1C) 128.44 (d, J=4.02 Hz, 1C) 130.66-130.81 (s, 1C) 130.81-131.06 (s, 1C) 132.18 (d, J=3.45 Hz, 1C) 159.86 (d, J=254.03 Hz, 1C). IR: (KBr) 3088, 3077, 3040, 2982, 2250, 1571, 1508, 1439, 1248 cm-1.Anal. Calcd for C8H5BrFN: Calc.C,44.89; H, 2.35; N, 6.54; F, 8.88; Found: C, 44.94; H, 2.73; N, 6.56; F, 8.73.

The chemical industry reduces the impact on the environment during synthesis 170572-49-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/111858; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

198633-76-0, name is 2-Fluoro-6-methylbenzonitrile, 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. 198633-76-0

To a cooled (0 OC) solution of 2-fluoro-6- methylbenzonitrile (5.0 g, 37 mmol) in 100 m of concentrated H2504 was added NBS (6.93 g,38.9 mmol). Then the mixture was stirred at O OC for 3 hrs and poured into ice-water (1 L). The solution was extracted three times with EtOAc (200 mL) and the combined orgianc layers werewashed with water and brine, dried oyer anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel fash chromatography to giye title compound.

Statistics shows that 198633-76-0 is playing an increasingly important role. we look forward to future research findings about 2-Fluoro-6-methylbenzonitrile.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DE JESUS, Reynalda, Keh; DING, Fa-xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; SHAHRIPOUR, Aurash; PIO, Barbara; TANG, Haifeng; WALSH, Shawn; WO2014/126944; (2014); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

105942-08-3, 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 105942-08-3 as follows.

Step 1: To a three-necked flask equipped with a Dean-Stark separator was charged phenol (6.17 g, 65.63 mmol), potassium carbonate (17.28 g, 125 mmol), DMF (62.5 mL) and toluene (62.5 mL) under a nitrogen atmosphere. After refluxing for 4 hours, dehydration treatment was carried out until it was confirmed that no water was produced in the system. Thereafter, toluene (50 mL) was removed using a Dean-Stark separator. After returning to room temperature, 12.5 g of 4-bromo-2-fluorobenzonitrile (62.6 mmol) was added, and the mixture was refluxed under nitrogen for 4 hr. After completion of the reaction, 100 mL of toluene was added to the solution to dilute the solution, and the solution was filtered through celite, and the obtained filtrate was washed twice with a sep. funnel, dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The solvent is obtained to obtain a crude crystal product, which is purified by a column to obtain an intermediate.

According to the analysis of related databases, 105942-08-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Normal University; Dong Yongqiang; Xiang Xueqin; (13 pag.)CN108997299; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

3939-09-1,Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

To a solution of methyl 1H-1,2,4-triazole-3-carboxylate (27 g, 215 mmol) in dimethylformamide (170 mL) was added sodium hydride (5.53 g, 95%, 217 mmol) and the mixture was stirred for 30 min. Added to this was 2,4-difluorobenzylnitrile (30 g, 217 mmol) and the resulting mixture stirred at room temp for 60 h. The mixture was diluted with water and filtered to remove solids. The solution was extracted with ethyl acetate and the organic layer was washed with water (3X’s) and brine, then dried (Na2SO4) and concentrated. The resulting residue was purified by flash chromatography (SiO2) eluting with 30% tetrahydroftiran/20% CH2Cl2/50% hexane to give the title compound as white needles (5.34 g, 10% yield). 1H-NMR (300 MHz, CDCl3) delta ppm: 8.92 (1H, s), 7.85 (1H, dd, J=8.8, 5.5 Hz), 7.67 (1H, dd, J=8.8, 2,6 Hz), 7.34-7.27 (1H, m), 40.3 (3H, s). LCMS [M+H]+ calcd for C11H8N4FO2: 247.06; found: 247.11.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3939-09-1, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

117482-84-5, A common compound: 117482-84-5, name is 3-Chloro-4-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

4.67 g (30 mmol) 3-chloro-4-fluoro-benzonitrile and 4.27 g (30 mmol) N-1-acetyl-[1,4]diazepan are stirred in 5.0 ml DIPEA for 6 hours at 90 C. Then the mixture is evaporated down i. vac. and the residue is dissolved in dichloromethane. The organic phase is washed twice with water, dried over sodium sulphate and evaporated down i. vac. The residue is further reacted without any more purification. Yield: 7.50 g (90%) Rf value: 0.20 (silica gel; dichloromethane/ethanol=50:1)

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, 3-Chloro-4-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/203078; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

1735-53-1, Name is 4-Bromo-3-(trifluoromethyl)benzonitrile, 1735-53-1, 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.

Dissolved aryl halide (1.0 equiv) in dry DMF and subjected to degassing with a gaseous mixture of (H2 + N2) balloon for three times. Added PdCl2(PPh3)2 (10 mol %) followed by Cul (8 mol%) at r.t. Added terminal alkyne (1.0 equiv. followed by TEA. The reaction mixture stirred at 50 C or 90 C. After cooling to room temperature, the resulting solution was subjected to rotary evaporation and partitioned between EtOAc and D.I. water. Aqueous layer was extracted with EtOAc 20 mL (3x). Combined organic layers were given water, brine washes and dried over anhydrous a2S04. After evaporation of the solvent, column chromatography on silica gel afforded the desired product.

Statistics shows that 4-Bromo-3-(trifluoromethyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 1735-53-1.

Reference:
Patent; LYNCH, Kevin; SANTOS, Webster; (353 pag.)WO2016/54261; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 198633-76-0 name is 2-Fluoro-6-methylbenzonitrile, 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. 198633-76-0

Commercially available 2-fluoro- 6-methylbenzonitrile (Apollo Scientific, 15.0 g, 1 1 1 mmol) was dissolved in triflic acid (75 mL) at 0 C then NBS (20.7 g, 1 17 mmol) was added. The reaction mixture was stirred at RT for 1 h then poured into ice water and extracted twice with DCM. The organic layer was washed with brine, dried over Na2S04, then filtered and evaporated to dryness to yield 3-bromo-6-fluoro-2- methylbenzonitrile: LC-MS: M+l= 216.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-6-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PIO, Barbara; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; WALSH, Shawn; WO2013/90271; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

60702-69-4, These common heterocyclic compound, 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, 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.

Synthesis of tert-butyl N-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]carbamate Into a 50.0-mL round-bottom flask, was placed tert-butyl N-[(1r,4r)-4-hydroxycyclohexyl]carbamate (500.0 mg, 2.32 mmol, 1.00 equiv), N,N-dimethylformamide (10.0 mL), sodium hydride (82.8 mg, 3.45 mmol, 1.50 equiv), 2-chloro-4-fluorobenzonitrile (432.6 mg, 2.78 mmol, 1.20 equiv). The resulting solution was stirred for 2 hours at 0 C. in a water/ice bath. The reaction was then quenched by the addition of 20.0 mL of water. The resulting solution was extracted with ethyl acetate (40.0 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride (40.0 mL). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2). The collected fractions were combined and concentrated under vacuum. This resulted in 470.0 mg (58%) of tert-butyl N-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]carbamate as yellow oil. LC-MS (ES+): m/z 295.0 [MH+], tR=1.199 min, (1.90 minute run).

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 60702-69-4.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts