Author: Jessica.F

Synthetic Route 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.

A mixture of 100 mg (0.46 mmol) 4-bromo-2,5-difluoro-benzonitrile, 146 mg (0.78 mmol) intermediate 111.14, 0.2 ml (1 .42 mmol) DIPEA and DMSO is heated to 100C for 5.5 h. After cooling to RT the reaction mixture is diluted with ACN and water and purified by HPLC giving rise to 1 16 mg 4-bromo-2-[4-(4-cyanophenyl)piperazin-1 -yl]- 5-fluoro-benzonitrile

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; BLUM, Andreas; PETERS, Stefan; (80 pag.)WO2017/148518; (2017); 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 4354-73-8 as follows. Recommanded Product: 4354-73-8

General procedure: Knoevenagel adduct 1 and 2 equivalents of a propargyl bromide derivative 2 were dissolved in anhydrous DMF (0.5 M with respect to the limiting reagent). Finely ground K2CO3 (3 equivalents) was then added to the solution and stirred at room temperature until the limiting reagent was consumed (monitored by TLC; 30 min-2 hrs.). The solution was then diluted with EtOAc and washed with H2O five times. The organic layer was then washed with brine and dried with Na2SO4. The solvent was removed under reduced pressure and the crude material purified via column chromatography (hexane-ethyl acetate) unless otherwise noted. Using the foregoing method, compounds 3a-3f and 3h-3m were prepared, and are described in further detail herein below Pale yellow oil, 93% yield, 2.34 g. Purified using 10% EtOAc in hexane. 1H NMR (500 MHz, CDCl3) delta 6.30 (dq, J=3.8, 2.0 Hz, 1H), 2.97 (d, J=2.6 Hz, 2H), 2.35 (t, J=2.5 Hz, 1H), 2.23-2.11 (m, 5H), 1.79-1.72 (m, 2H), 1.63 (pd, J=6.9, 6.2, 4.1 Hz, 2H). 13C NMR (125 MHz, CDCl) delta 131.0, 127.0, 113.9, 75.2, 74.9, 43.4, 28.8, 25.4, 24.5, 22.3, 21.3. HRMS (ESI-TOF) m/z: [M+H]+ Calcd for C12H13N2 185.1073; Found 185.1080. [M+Na]+ Calcd for C12H12N2Na 207.0893; Found 207.0883. Rf=0.51 (20% EtOAc in hexane)

According to the analysis of related databases, 4354-73-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Florida Research Foundation, Inc.; Grenning, Alexander James; Scott, Sarah; (66 pag.)US10287239; (2019); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 39095-25-5,Some common heterocyclic compound, 39095-25-5, name is 2,5-Dimethylterephthalonitrile, molecular formula is C10H8N2, 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 100ml 4-neck reactor 2,5-dimethyl-terephthalonitrile 2.3g, Carbon tetrachloride 23ml, NBS 5.3g, AIBN 0.07g 1 hour reaction at charged 75C It was. After completion of the reaction, it was allowed to cool to room temperature. Wash the residue and the reaction solution was filtered with carbon tetrachloride It was. Crude product is obtained in the oil and the filtrate was concentrated. The addition of methanol and allowed to crystallize the crude product. Taken out crystals were filtered off, 1,4-dicyano-2,5-bis-bromo methyl benzene was obtained 0.57g. In 50ml 3-necked reactor 1,4-dicyano-2,5-bis bromomethylbenzene 0.55g, Triethyl phosphite 0.61g was stirred and heated to charged 100-110 . At this temperature the reaction was carried out for 2 hours. Was allowed to cool to room temperature, and purified on a silica gel column 2,5-dicyano-1,4-bis (diethyl phosphonyl methyl) benzene was obtained 0.45g. 50ml 3-necked reactor to 2,5-dicyano-1,4-bis (diethyl phosphonyl methyl) benzene 0.45g, DMF (dehydration) 15ml, 4 formylpyridine 0.28g They were charged. After nitrogen substitution, Potassium t- butoxide 0.35g It was changed to green-brown solution and dropping the 5mlDMF solution slowly. It was allowed to react for 3 hours at 60 . The reaction mixture was extracted with chloroform and released into the water. The reaction mixture was concentrated to give crude product. The crude product was purified on a silica gel column (toluene / acetone 1/1) and the resulting solid to yield 0.08g of intermediate 45 and purified construed methanol. A synthesis flow of this intermediate 45 below

The synthetic route of 39095-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RICOH COMPANY LIMITED; YAMADA CHEMICAL COMPANY LIMITED; HIRANO, SHIGENOBU; YASHIRO, TOHRU; MANABE, YOUSUKE; HAYASHI, SATOSHI; (35 pag.)JP5900813; (2016); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 2286-54-6, A common heterocyclic compound, 2286-54-6, name is 3,3-Diphenylpropanenitrile, molecular formula is C15H13N, 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 the glove box, 0.01 mmol of nickel chloride was added, 0.52 mmol of diphenylphosphine oxide, 1.5 equivalents of t-BuOK (potassium tert-butoxide),Add to the Schlenk reaction tube in turn, then Add 0.4mmol 1, 1-diphenylpropionitrile compound, Vacuum and backfill nitrogen; under a nitrogen atmosphere, add 3 ml of 1,4-dioxane to the solvent. The reaction was continued at 120 C for 16 h. After the reaction is completed, it is cooled to room temperature and separated by column chromatography. That is the target product: 1,1-diphenylethyldiphenylphosphine oxide, yield 87%.

The synthetic route of 2286-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University; Zhang Jishu; Qi Tafamingrenqingqiubugongkaixingming; (13 pag.)CN109438512; (2019); 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. 906673-45-8, name is 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(4-Bromo-3-(hydroxymethyl)phenoxy)benzonitrile

4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile (compound B) (10.0 g, 32.9 mmol), potassium acetate (9.7 g, 99.0 mmol), XPhos (0.078 g, 0.16 mmol), XPhos-Pd-G2 (0.068 g, 0.082 mmol) and tetrahydroxydiboron (4.4 g, 49.3 mmol) were added to an oven dried glass reactor with a positive N2 pressure. The vessel was sealed and then evacuated and backfilled with N2 (four times). MeOH (100 mL, degassed) was added via syringe, followed by the addition of ethylene glycol (5.5 mL, 99.0 mmol). The reaction was then heated to 64-66 C until the starting material was consumed (as monitored by TLC). The solvent was concentrated in vacuo and the crude reaction product was dissolved in EtOAc (50 mL) and then transferred to a separatory funnel. H20 was added (50 mL), the layers were separated and the aqueous layer was further extracted with more EtOAc (30 mL). The combined organic layers were washed once with 1 M HCI (30 mL) and once with H20 (30 mL), then dried over Na2S04 and concentrated in vacuo. The solid residue was purified twice by recrystallization in hot methanol, thus affording pure 4-[(1-hydroxy-1 ,3-dihydro- 2,1-benzoxaborol-5-yl)oxy]benzonitrile (crisaborole) (6.6 g, 26.3 mmol) as a white solid. Yield: 80% (calculated from 4-(4-bromo-3-(hydroxymethyl)phenoxy)benzonitrile) Purity by HPLC: > 99.9% 1H-NMR (200 MHz, DMSO-d6, delta ppm): 9.22 (1 H, s); 7.85-7.83 (2H, m, J= 8.9 Hz); 7.81 -7.79 (1 H, d, J= 8.1 Hz); 7.15-7.13 (3H, m); 7.10-7.08 (1 H, dd, J= 8.1 , 2.1 Hz); 4.97 (2H, s) 13C-NMR (50 MHz, DMSO-d6, ppm): 160.6; 157.1 ; 156.6; 134.7; 132.6; 1 18.9; 1 18.6; 1 12.7; 105.5; 69.7.] FT-IR: 2222.9, 1600.8, 1501.2, 1467.5, 1406.0, 1390.9, 1360.6, 1244.7, 1 167.3, 1 1 16.1 , 1010.7, 937.3, 892.5

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; LABORATORIOS LESVI, SL; HUGUET CLOTET, Juan; OZORES VITURRO, Lidia; RODRIGUEZ ROPERO, Sergio; DALMASES BARJOAN, Pere; (39 pag.)WO2018/115362; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 32446-66-5, 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. 32446-66-5, name is 4,4′-Dicyanobenzophenone, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 3 4-[alpha-(4-Cyanophenyl)-alpha-hydroxy-5-thiazolylmethyl]-benzonitrile Analogously to Example 1, the title compound is prepared starting from 0.512 ml of diisopropylamine, 2.44 ml of a 1.6M n-butyllithium solution, 530 mg of 2trimethylsilylthiazole and 603 mg of 4,4′-dicyanobenzophenone in THF at -70 and with working up in the same manner. Purification of column chromatography (SiO2, hexane/ethyl acetate 2:2) yields the title compound in pure for. TLC (hexane/ethyl acetate 2:2) Rf =0.2; 1 H-NMR (CDCl3): delta(ppm)=4.39 (s,1H), 7.42 (d,1H), 7.54 and 7.7 (m,8H), 7.88 (d,1H).

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

Synthetic Route of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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.

To a suspension of sodium hydride (4.04 g, 100 mmol, 60 % purity) in THF (25 mL) was added tert-butyl N-(2-hydroxypropyl)carbamate (8.84 g, 50.5 mmol) at 0 “C. The resulting mixture was stirred at 0 C for 0.5 h, then a solution of 4-bro mo-2,5-difluorobenzonitrile (10 g, 45.9 mmol) in THF (25 mL) was added. The mixture was stirred at 0 C for 0.5 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 50/1 to 10/1 ) to give the desired product (13 g, 34.8 mmol, 76% yleld) as a white solid.MS (M+H+): 397.11H NMR (400 MHz, CDCI3) delta [ppm]: 7.33-7.30 (t, J = 6Hz, 1 H), 7.27-7.24 (t, J = 6Hz, 1 H), 4.99 (s, 1 H), 4.57 (s, 1 H), 3.53-3.48 (m, 1 H), 3.33-3.28 (m, 1 H), 1 .62-1 .45 (q, 9H), 1.36-1.26 (m, 3H).

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.

1349718-98-4, name is 2,4-Dichloro-6-fluorobenzonitrile, 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. SDS of cas: 1349718-98-4

To a solution of 2,4-dichloro-6-fluorobenzonitrile (3.87 mmol) in 15 mL THF was added a solution of BH3 (15.5 mmol, 1M in THF) and the mixture was stirred at 60 C. for 1 h. After cooling to 0 C., water was added followed by MeOH and the mixture was then heated to 70 C. for 10 min. The solvent was evaporated, the residue was taken up in water and EtOAc. The aqueous phase was separated, basified with 1M NaOH and it was extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to obtain the desired product as yellow oil. LC-MS (A): tR=0.39 min; [M+CH3CN+H]+: 234.90.

The synthetic route of 1349718-98-4 has been constantly updated, and we look forward to future research findings.

Related Products of 191014-55-8, The chemical industry reduces the impact on the environment during synthesis 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of (4S,5S)-4-hydroxy-5-methylpyrrolidin-2-one 7 33 (7.00 g, 60.8 mmol) in THF (120 mL) was added sodium bis(2-methoxyethoxy)aluminium dihydride (70% in toluene, 59.7 mL, 215 mmol) slowly at 5 C. After stirring at 70 C for 3 h, the reaction mixture was cooled to 5 C followed by addition of sodium carbonate decahydrate (26.1 g, 91.2 mmol). The mixture was stirred at room temperature for 16 h, diluted with THF, and the precipitate was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in DMSO (80 mL). To the solution was added lithium carbonate (8.99 g, 122 mmol) and 2-chloro-4-fluorobenzonitrile (9.46 g, 60.9 mmol), and the mixture was stirred at 100 C for 1 h. The mixture was diluted with EtOAc and H2O, and the organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc) to give 10 (10.7 g, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3) delta: 1.18 (3H, d, J = 6.6 Hz), 1.82 (1H, d, J = 5.5 Hz), 2.01-2.14 (1H, m), 2.25-2.35 (1H, m), 3.19-3.28 (1H, m), 3.43-3.51 (1H, m), 3.89-3.98 (1H, m), 4.43-4.52 (1H, m), 6.43 (1H, dd, J = 8.9 and 2.4 Hz), 6.56 (1H, d, J = 2.4 Hz), 7.42 (1H, d, J = 8.9 Hz). MS (ESI) m/z 237 [(M+H)+].

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, 4-Fluoro-2-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.