Author: Jessica.F

Electric Literature of 16588-02-6, A common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

1st Step Hydrazine monohydrate (4.87 ml) was added to an EtOH (19 ml) solution containing 2-chloro-5-nitrobenzonitrile (1.83 g), followed by stirring for 0.5 hour under ice cooling. Water was added to the reaction solution, and a solid precipitate was collected by filtration and washed with IPE and ethyl acetate. A red solid of 5-nitro-1H-indazol-3-amine (1.45 g) was thus obtained. MS (ESI m/z): 179 (M+H)

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJIFILM Corporation; FUJIWARA, Hideyasu; MIZUMOTO, Shinsuke; KUBO, Yohei; NAKATA, Hiyoku; HAGIWARA, Shinji; BABA, Yasutaka; TAMURA, Takashi; KUNIYOSHI, Hidenobu; MASHIKO, Tomoyuki; YAMAMOTO, Mari; US2014/309225; (2014); A1;,
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Reference of 501-00-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(3-fluorophenyl)acetonitrile (6.000 g, 44.398 mmol) and sodium hydride (2.344 g, 97.676 mmol) in N,N-dimethylformamide (200 mL) at 0 C to this mixture 1,3-dibromopropane (4.504 mL, 44.398 mmol) was added and after stirring at 50 C for 17 hours, the temperature was lowered to room temperature, and a saturated sodium bicarbonate aqueous solution (10 mL) was added to the reaction mixture at 0 C and stirred for 10 minutes to complete the reaction. The solvent was removed from the reaction mixture under reduced pressure, the obtained concentrate was poured into water and extracted with hexane. 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 (4.270 g, 54.9%) as a colorless oil.

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, 2-(3-Fluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

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;,
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Electric Literature of 96606-37-0, These common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, 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.

In analogy to GP 2, 1 g of 2,4,6-trifluoro-benzonitrile (6.37 mmol; 1 eq.; commercially available) and 2.26 g 2-fluoro-4-iodo-benzenamine (9.55 mmol, 1.5 eq; commercially available) were dissolved in 100 ml of THF. The mixture was cooled to -65 C; 2.14 g of potassium tert-butoxide (19.1 mmol, 3 eq; commercially available) were added. The mixture was stirred for 35 min at this temperature and another 21 h at RT. The mixture was stirred into 120 ml of ice water and extracted three times with ethyl acetate (100 ml each). The combined organic layers were washed with brine, dryed over sodium sulfate and concentrated to afford 4.137 g of crude product. Purification was achieved by flash chromatography (hexane/ethyl acetate) to afford 646 mg (27.13% yield; 1.73 mmol) of the target compound.

The synthetic route of 96606-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; BAYER HEALTHCARE AG; WO2008/138639; (2008); A1;,
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Synthetic Route of 1114546-30-3,Some common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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.

A mixture of 4-bromo-2-fluoro-3- methylbenzonitrile (7.0 g, 32.7 mmol), potassium vinyltrifluoroborate (5.3 g, 39.3 mmol), Pd(dppf)Cl2 (0.5 g, 0.7 mmol) and TEA (30 mL) in EtOH (70 mL) was refiuxed under Ar for 4 hours. After being cooled to room temperature, the reaction mixture was concentrated and the residue was purified by column chromatography (petrol ether : EtOAc = 10 : 1) to afford 2- fluoro-3-methyl-4-vinylbenzonitrile as a white solid.

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 36282-26-5, category: nitriles-buliding-blocks

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25.00 mmol), bis(pinacolato)diboron (9.52 g, 37.5 mmol), potassium acetate (7.36 g, 75.0 mmol), in dioxane (50 mL) argon was purged for 5 mins. PdCl2(dppf)-CH2Cl2 adduct (12.25 g, 15.00 mmol) was added and argon was bubbled through the reaction mixture and heated at 94 C (silicon oil bath) for 14 h. The reaction mixture was cooled to RT, filtered through celite pad, washed with ethyl acetate (200 mL). The organic layer was washed with water (100 mL) and the aq. layer was separated and re-extracted with ethyl acetate (2 x 100 mL). Combined organic extracts were washed with brine, dried over sodium sulfate and solvent was removed under reduced pressure to give the brown colored crude product. The product was purified by silica gel column chromatography using ethyl acetate in pet ether as an eluant to afford 89A (4 g, 16.19 mmol, 64.8 % yield) as a off- white semi solid. NMR (400 MHz, CDC13) d 7.89-7.93 (m, 1H), 7.54-7.59 (m, 1H), 7.39-7.50 (m, 1H).

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); 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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, A new synthetic method of this compound is introduced below., HPLC of Formula: C13H16N2O2

General procedure: To a round-bottom flask equipped with a stir bar was added 28a-b (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (10 mL/mmol). The reaction was refluxed and stirred in a pre-heated 75 C. oil-bath for 6 h. After cooling to room temperature, the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo and further purified on a silica gel column. Example 89 Synthesis of 215 tert-Butyl (E)-(4-(N?-hydroxycarbamimidoyl)benzyl) carbamate (29a) (0246) The synthesis follows the general procedure described in Example 88. Yield: 65%. MP: 142-145 C. 1H NMR (400 MHz, DMSO-d6) delta 9.57 (s, 1H, -OH), 7.61 (d, J=8.1 Hz, 2H, -ArH), 7.40 (t, J=6.1 Hz, 1H, -NHCO-), 7.22 (d, J=8.1 Hz, 2H, -ArH), 5.77 (s, 2H, -NH2), 4.13 (d, J=6.1 Hz, 2H, -ArCH2-), 1.40 (s, 9H, -CH3).

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; Washington University; Tu, Zhude; Rosenberg, Adam; Liu, Hui; Han, Junbin; US2019/2450; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1953-99-7, Application In Synthesis of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

To a boiling solution of lithium 1-hexanolate in 1-hexanol, prepared via dissolving 0.1 g oflithium in 20 ml of anhydrous 1-hexanol, added compound 3 (0.7 g, 2 mmol) and compound5 (0.53, 2 mmol). After 5 h, the reaction mixture was cooled and mixed with 50 ml of acetoneand 5 ml of acetic acid. Then reaction mixture was concentrated at rota evaporator, purifiedby silica gel column chromatography usingDCM:CH3OH(20:1) as an eluent to obtain an oilybluish green compound as a major fraction, To this compound Zn(OAc)2·2H2O (0.13 g, 0.6mmol), and 20 ml of DMF added and heated at reflux for 1 h. After cooling, to the reactionmixturewas added 100ml of water and 100ml of chloroform. The organic layer was separated,washed with 100ml of water, then reaction mixture was concentrated at rota evaporator, purifiedby silica gel column chromatography using DCM:CH3OH (20:1) as an eluent to obtainoily bluish green compound 6 (0.368 g, 52.5percent). IR (KBr tablet) numax/cm?1: 3018, 2956, 2857,1597, 1492, 1265, 1214, 1154, 1092, 971, 745. 54H18Cl8F6N84Zn; Calculated, percent: 49.67; H1.39; N 8.58; O 4.9, Found, percent: 49.89; H 1.42; N 8.48; O 4.93. UV-Vis: nm (log epsilon): in CHCl3;660(102),715(142),815(45). MALDI-TOF-MS: m/z calcd for 54H18Cl8F6N84Zn, 1303.81;found 1304.74 [M + H+]+.

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; Jeong, Jaemyeng; Kumar, Rangaraju Satish; Kim, Ick Jin; Son, Young-A; Molecular Crystals and Liquid Crystals; vol. 644; 1; (2017); p. 249 – 256;,
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Synthetic Route of 1897-52-5, These common heterocyclic compound, 1897-52-5, name is 2,6-Difluorobenzonitrile, 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.

I. Synthesis Examples; Example 1.1 : 2-Difluoromethoxy-6-prop-2-ynylsulfamoyl-thiobenzamide (4); 1.1. 2-Fluoro-6-methoxybenzonitrile:; 640.5 g (4.6 mol) of difluorobenzonitrile have been dissolved in 3.5 I of methanol and then cooled to 0-5 C. 828.8 g of 30% strength sodium methoxide solution have been added dropwise in this temperature range, and the reaction mixture has been stirred at room temperature overnight. Then the reaction mixture has been added to 20 I of water and the precipitate has been filtered off with suction and washed twice with water and twice with heptane. The solid has been dried in vacuo at 50 C to yield 740 g (455 mmol) of the title compound as a white solid.

The synthetic route of 1897-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; WO2007/93530; (2007); 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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Trifluoromethyl)phenylacetonitrile

Step 1: Preparation of Intermediate 2-(4-Trifluoromethyl-phenyl)-ethylamine (I-16a) (4-Trifluoromethyl-phenyl)-acetonitrile (2 g, 10.81 mmol) in methanolic ammonia (50 mL) was added to Raney nickel (400 mg) in methanol taken in a parr hydrogenator. The flask was stirred at 50 PSI overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mixture was filtered through celite bed and the filtrate was dried under reduced pressure to afford 2 g of the product (97.89% yield). LCMS purity: 98.73%, m/z=190.0 (M+1)

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; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); A1;,
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Related Products of 57381-51-8, 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 14 2-(4-Chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole To a solution of 4-chloro-2-fluoro-benzonitrile (1 g, 6.428 mmol) in ethanol (10 mL) were added sodium ethoxide solution (4.8 mL, 12.86 mmol, 21% wt in ethanol). The reaction mixture was heated at gently reflux for 12 h. The solvent was removed and the residue was partitioned between water (10 mL) and diethyl ether (20 mL). The layers were separated and the product was extracted with diethyl ether (20 mL). The organic layers were washed with brine (5 mL) and dried over anhydrous sodium sulfate. The solid was filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 5% ethyl acetate in hexanes yielded 4-chloro-2-ethoxy-benzonitrile (670 mg, 57%). Hydrogen chloride gas was passed through a solution of 4-chloro-2-ethoxy-benzonitrile (670 mg, 3.689 mmol) in anhydrous ethanol (25 mL) cooled to 0 C. After 45 min, the hydrogen chloride gas was stopped and the reaction vessel was sealed with a Teflon stopper. It was stirred at room temperature for 5 d. The reaction vessel was cooled to 0 C. and the stopper was removed. The solvent was removed and the residue was triturated in diethyl ether to afford ethyl 4-chloro-2-ethoxy-benzimidate hydrochloride (913 mg, 94%). It was used without further purification. To a solution of meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine (810 mg, 2.879 mmol) and ethyl 4-chloro-2-ethoxy-benzimidate hydrochloride (913 mg, 3.455 mmol) in ethanol (10 mL) was added triethylamine (605 muL, 4.319 mmol). The reaction mixture was heated at gentle reflux for 4 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 70% ethyl acetate in hexanes to afford 2-(4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole (1.045 g, 81%). HR-MS (ES, m/z) calculated for C23H20N2OCl3 [(M+H)+]445.0636, observed 445.0644.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoffmann-La Roche Inc.; US6617346; (2003); B1;,
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