Tag: M.W=200-300

Related Products of 179897-89-3, A common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

General procedure: Into an oven-dried flask equipped with a magnetic stir bar was added aryl fluoride (1.00 g, 1.0 eq.), Na2S (1.1 eq.) and DMF (5 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. Then 1 M NaOH (50 mL) was added and was washed with CH2Cl2 (2 x 25 mL). The aqueous layer was acidified to pH ~ 1-2 with 6 N HCl and extracted with CH2Cl2 (2 x 50 mL). The combined organic layer was washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to provide a crude residue. To the residue was added 10% HCl (40 mL) and cooled with an ice-water bath. Then zinc dust (4 g) was added and the mixture was stirred for 1 h. Then EtOAc (100 mL) was added and the mixture was stirred for an additional 30 minutes. The organic layer was separated and washed with water (40 mL) and brine (40 mL), dried over MgSO4, filtered and concentrated to provide the desired product with satisfactory purity.

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taldone, Tony; Patel, Pallav D.; Patel, Hardik J.; Chiosis, Gabriela; Tetrahedron Letters; vol. 53; 20; (2012); p. 2548 – 2551;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Safety of 5-Bromo-2-fluorobenzonitrile

II1 (1.0 g, 5 mmol) was dissolved in DMF (15 mL)K2CO3 (2.0 g, 15 mmol), tetrahydropyrrole (1.0 g, 15 mmol)The response was complete at 6C for 6 h at 86 C. Add 80 mL of water to dilute,Ethyl acetate (80 mL x 3), washed with saturated brine, dried over anhydrous magnesium sulfate,The solvent was evaporated under reduced pressure to give 1.1 g of an orange solid, 5-bromo-2-tetrahydropyrrole-benzonitrile (III7) in a yield of 97.3%.

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; Zhang Lei; Wu Fangping; Li Jing; Zou Yake; (15 pag.)CN106632245; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 105942-08-3, name is 4-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-fluorobenzonitrile

a 4-Bromo-2-methoxybenzonitrile A suspension of potassium methoxide (4.24 g, 60.0 mmol) in tetrahydrofuran (40 mL) was added in portions to a solution of 4-Bromo-2-fluorobenzonitrile (8.0 g, 40.0 mmol) in tetrahydrofuran (50 mL) at -50° C. After one hour, the dry ice bath was removed and the reaction mixture was allowed to warm up to room temperature and stirred at room temperature for 6 hours. The reaction mixture was poured onto water (250 mL) and the solid was collected by filtration to give 4-bromo-2-methoxybenzonitrile (7.85 g, 92percent). 1H NMR (DMSO-d6) delta 3.94(s, 3H), 7.32 (d, J=8.23 Hz, 1H), 7.15 (s, 1H), 7.69 (d, J=8.23 Hz, 1H).

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; Abbott Laboratories; US2002/156081; (2002); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 105942-08-3, A common heterocyclic compound, 105942-08-3, name is 4-Bromo-2-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

A mixture of 4-bromo-2-fluoro-benzonitrile (15.0 g, 75.0 MMOL), methanol (30.4 mL, 350 MMOL) and potassium carbonate (31.1 g, 225 MMOL) in DMF (150 mL) was stirred under argon at 55 °C overnight. At this point TLC (100percent methylene chloride) revealed no starting material, and the reaction mixture was poured into ether (300 mL) and water (150 mL). The layers were separated, and the organic layer was washed with water (150 mL) and brine (50 mL), dried over MG2S04, filtrated, and concentrated under reduced pressure, providing (15.2 g, 95.5percent) OF 4-BROMO-2-METHOXY-BENZONITRILE AS a white SOLID. H-NMR (CDCI3) 8 7.41 (d, J = 8.1 Hz, 1H), 7.16 (dd, J = 8.1, 1,6 Hz, 1H), 7.13 (d, J = 1,6 Hz, 1H), 3.93 (s, 3H); MS GC-MS (M+ = 211; RT= 6.15 min).

The synthetic route of 105942-08-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2005/14566; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 134604-07-2, A common heterocyclic compound, 134604-07-2, name is 1-Cyano-2-bromo-5-nitrobenzene, molecular formula is C7H3BrN2O2, 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.

Description for D422-(2-methylpropyl)-5-nitrobenzonitrile (D42)To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D42) (11 g) as a light yellow oil. deltaEta (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1H, dd), 8.51 (1H, d).

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; GLAXO GROUP LIMITED; LIN, Xichen; REN, Feng; ZHANG, Haibo; WO2011/113309; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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., Application In Synthesis of 2-Bromo-4-fluorobenzonitrile

4I-(Benzyloxy)-5-fluorobiphenyl-2-carbonitriIe (CAB06048) A mixture of 2-bromo-4-fluorobenzinitrile (4.50 g, 22.5 nimol), 4- benzyloxyphenylboronic acid (5.19 g, 22.76 mmol), dimethoxyethane (25 mL) and 2M Na2CO3 (40 mL) was heated to reflux before Pd2(dba)3 (0,05 g, 0.055 mmol) was added and heating was continued for 5 hours. After cooling to room temperature CHCl3 (ca. 100 mL) was added to dissolve the product, which crystallised from the organic layer. The mixture was filtered through celite, the organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure. The residue was recrystallized from CHCl3/hexane to give CAB06048 (532 g, 78%) as colorless needles. Mp. 94-96 0C; 1H NMR (400 MHz, DMSO-^6) delta 5.12 (s, 2H), 7.06-7.12 (m, 3H), 7.18 (dd, J= 9.4, 2.7 Hz, IH)5 733-7,53 (m, 7H)5 7.74 (dd, J = 8.6, 5,7 Hz, IH); LRMS (ES+): m/z 326.4 (100%, [M+Naf), 3043 (60%, [M+H]+); HRMS (ES+) calcd for C20Hi5FNO [M+H]+: 304.1132, found 304.1125.

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; STERIX LIMITED; WOO, Lok Wai Lawrence; BUBERT, Christian; WOOD, Paul Michael; PUTEY, Aurelien; PUROHIT, Atul; POTTER, Barry Victor Lloyd; WO2011/23989; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 1813-33-8 as follows. name: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

According to the analysis of related databases, 1813-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. SDS of cas: 57381-49-4

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 79630-23-2, 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. 79630-23-2, name is 3-Bromo-4-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-bromo-4-fluorobenzonitrile (1.0 equivalent), 2- (trifluoromethoxy) benzeneboronic acid (1.25 equivalent), palladium acetate (0.005 equivalent) and triphenylphosphine (0.01 equivalent) were sequentially charged to a multi-necked flask. After purging the flask with nitrogen, toluene (5ML/GRAM. of 3-bromo-4-fluorobenzonitrile) was added and the resulting slurry was stirred while bubbling nitrogen subsurface for about 20 minutes. In a separate flask, an aqueous potassium phosphate solution was prepared by dissolving solid potassium phosphate (2.0 equivalents) into water (2ML/GRAM of potassium phosphate). The resulting solution was de-oxygenated by bubbling nitrogen subsurface while stirring for about 30 minutes. The aqueous potassium phosphate solution was added to the toluene slurry and the reaction mixture was warmed to 60-65 C by heating with steam. The progress of the reaction was monitored by HPLC and the reaction temperature was held between 63-69 C. When 3-bromo-4- fluorobenzonitrile was consumed, heating was discontinued and the reaction mixture was cooled to RT using an ice bath. The aqueous layer was siphoned from the vessel and Ecosorb C-941 (0.5 GRAM/GRAMS of 3-bromo-4-fluorobenzonitrile, commercially available from Graver Technologies, Glasgow, Delaware) was added to the reaction vessel. The resulting black slurry was stirred at RT for 15 hours. The carbon was removed by filtering the slurry through a pad of solka flok on a filter pot. The filter cake was washed with toluene (4ML/GRAM of 3-bromo-4-fluorobenzonitrile). The combined filtrates were batch concentrated (40-50 C) to provide the biaryl nitrile product as a thick, light-orange oil (94.0% yield).

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

Reference:
Patent; MERCK & CO., INC.; WO2004/83189; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 85068-32-2, 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. 85068-32-2 name is 2-(3,5-Bis(trifluoromethyl)phenyl)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.

In a round bottom flask 1,3,5-Benzenetricarbaldehyde 1 (0.5 g,3.1 mmol) and trifluoromethyl substituted phenylacetonitrile 2(9.7 mmol) were taken in absolute ethanol (300 mL). Sodium ethoxide(0.80 g, 11.6 mmol) was added drop wise to the above solution.Under protection from air, the solution was heated to reflux for 3 h. Then, volatiles were removed under reduced pressure. Under protection from air, 200 ml of water was added to the residue. The mixture was repeatedly extracted with small portions (30 mL) of dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated under vacuum condition to leave the residue. The resulting residue was chromatographed on silica gel (Wako C-300) using dichloromethane/hexane (1:1) mixed solvent as an eluent to give the desired compound(1.9 g, 90% for 3a, 2.4 g, 88% for 3b) as pale yellow solids.Compound 3a, pale yellow solid, M.p. 231-232 C; 1H NMR(400 MHz, CDCl3) 7.72 (s, 3H, aryl H), 7.76 (d, 6H, aryl H, J = 7.3 Hz),7.86 (d, 6H, aryl H, J = 7.3 Hz), 8.48 (s, 3H, ethenyl H). EI-MS (75eV):m/z 663 (M+). Elemental analysis calculated for C36H18F9N3: C,65.16%; H, 2.73%; N, 6.33%. Found: C, 65.30%; H, 2.55%; N, 6.49%.Compound 3b, pale yellow solid, M.p. 249-251 C; 1H NMR(400 MHz, CDCl3) 7.79 (s, 3H, aryl H), 7.99 (s, 3H, aryl H), 8.16 (s, 6H,aryl H), 8.51 (s, 3H, ethenyl H).EI-MS (75eV): m/z 867 (M+).Elemental analysis calculated for C39H15F18N3: C, 53.99%; H, 1.74%;N, 4.84%. Found: C, 53.81%; H,1.85%; N, 4.64%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(3,5-Bis(trifluoromethyl)phenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Article; Moriguchi, Tetsuji; Yakeya, Daisuke; Jalli, Venkataprasad; Journal of Molecular Structure; vol. 1185; (2019); p. 403 – 409;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts