Category: 22236-10-8

22236-10-8, name is 4-(Difluoromethoxy)aniline, belongs to ethers-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. Application In Synthesis of 4-(Difluoromethoxy)aniline

The nitro ether (149 mmol) was dissolved in ethanol (37.5 mL), diluted with water (25 mL), and was treated with ammonium chloride (84.7 mmol) and iron powder (105 mmol). The reaction mixture was heated at reflux for 30 minutes and the suspension was filtered through Celite. The filter cake was washed with ethanol three times and the combined filtrates were concentrated. The residue was dissolved in water and the pH adjusted to 9-10 with 5 M sodium hydroxide. The aqueous layer was extracted with ethyl acetate (3×100 mL) and the combined organic layers were dried (magnesium sulfate) and concentrated to a yellow oil. The oil was dissolved in acetic anhydride (23.5 mmol) and the reaction mixture was maintained at rt for 16 h. The reaction mixture was diluted with water (50 mL) and was neutralized with solid sodium bicarbonate. The precipitated solids were isolated by filtration, washed with water, and dried to provide the acetamide in 62% yield as a light yellow solid.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xie, Wenge; Herbert, Brian; Ma, Jianguo; Nguyen, Truc Minh; Schumacher, Richard; Gauss, Carla Maria; Tehim, Ashok; US2005/250808; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: 22236-10-8

full text is not avalable from article

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:
Article; Nino, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernandez, Joan-Carles; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 7; (2016); p. 854 – 881;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, belongs to ethers-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 22236-10-8, Safety of 4-(Difluoromethoxy)aniline

To a mixture of 9 (190 mg, 0.74 mmol), 4-(difluoromethoxy)aniline (5a, 130.5 mg, 0.82 mmol) and 4-(dimethylamino)pyridine (DMAP) (99.4 mg, 0.81 mmol) in dimethylformamide (DMF) (3 mL) was added N’-ethylcarbodiimide hydrochloride (EDO HC1 (156 mg, 0.81 mmol), the mixture was stirred at room temperature for 1 h. Then, 100 mL water was added to the reaction mixture to form off-white precipitate, which was collected on a filter to give an off- white solid. The solid was dissolved in ethyl acetate and dried over MgS04, filtered, and the solvent was removed by rotary evaporator. The crude product was purified by recrystallization from ethyl acetate/hexane to afford 2a as white solid (120.4 mg, 41% yield): mp. 174- 177 C; 1H NMR (500 MHz, CDC13) delta 0.92 (t, J = 7.5 Hz, 3H), 1.64 (m, 2H), 2.06 – 2.22 (m, 2H), 2.42 (t, = 7.5 Hz, 2H), 2.49 (t, = 6.9 Hz, 2H), 3.31 (t, = 5.7 Hz, 2H), 6.01 (s, 1H), 6.45 (t, = 74.0 Hz, 1H), 7.07 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 8.6 Hz, 2H), 7.92 (s, 1H), 12.69 (s, 1H). 13C NMR (125 MHz, CDCI3) delta 13.8, 21.1, 24.8, 30.2, 35.5, 39.7, 107.8, 116.1(t, = 259 Hz), 120.6, 121.3, 135.6, 147.3, 160.2, 165.5, 169.9, 170.5; 19F NMR (376 MHz, CDCI3) delta -80.7; HRMS (ESI+) calcd for C18H22F2N3O3S [M + H]+ 398.1344, found 398.1345 (Delta = -0.03 ppm).

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

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; OJIMA, Iwao; ALFORD, Vincent; KAMATH, Anushree; CAO, Jian; REN, Xiaodong; SAMPSON, Nicole; AWWA, Monaf; (63 pag.)WO2018/175670; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 22236-10-8, The chemical industry reduces the impact on the environment during synthesis 22236-10-8, name is 4-(Difluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

The reaction is carried out under protective gas (argon). A mixture of 2.39 g (12 mmol) 1-(4-bromophenyl)ethanone, 0.99 mL (8 mmol) 4-(difluoromethoxy)aniline, 2.21 g (16 mmol) potassium carbonate, 150 mg (0.8 mmol) copper iodide and 180 mg (1.6 mmol) L-proline in 12 mL DMSO was stirred for 72 hours at 95 C. The reaction mixture was added to water, mixed with a little ammonia extracted twice with tert-butyl-methylether. The combined organic phases were dried on sodium sulphate and evaporated to dryness in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether+30% ethyl acetate). The product was further reacted directly.Yield: 33% of theoryC15H13F2NO2 (277.27)Rt=1.98 min. method 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, 4-(Difluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2010/240669; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H7F2NO

General procedure: N-substituted benzylidene pyrrolidine dione (0.5 mol),0.6 mmol TBTU, and 0.6 mmol EDCI were dissolved in 2mL DCM and 0.75 mmol DIEA mixture solution and stirred for 30 min. Next, 0.5 mol of amine or methylamino acid in DCM (8 mL) solution was slowly added to the solution and stirred at room temperature for 4-10 h with the TLC monitoring reaction. After the reaction was complete, the resultant solution was washed with dilute hydrochloricacid and saturated sodium bicarbonate solution, then dried with anhydrous sodium sulfate, followed by column chromatography separation. The target product was obtained by crystallization.The yield ranged from 72 to 90%.

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.

Electric Literature of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

In a 20 mL four-necked flask, 4-(difluoromethoxy)aniline (0.5 g, 3.14 mmol) and hydrochloric acid (37% in water, 0.54 ml, 6.6 mmol) were combined with water (5 ml) to give a light yellow solution. Cooled to 0 C using an ice-bath, sodium nitrite (217 mg, 3.14 mmol) was dissolved in water (1 ml) and added carefully ensuring that the temperature did not increase above 5 C. Sodium azide (204 mg, 3.14 mmol) was dissolved in water (1 ml) and added drop-wise to the orange solution, keeping the temperature below 5 C. The reaction mixture was cooled at 0-5 C for 1 hour and an orange emulsion was observed. The layers were separated using TBME and the organic layer was washed with brine, dried over sodium sulphate and filtered. The filtrate was concentrated under vacuum to yield l-azido-4-(difluoromethoxy)benzene as an orange liquid. In a 50 ml round-bottomed flask, l-azido-4-(difluoromethoxy)benzene (540 mg, 2.92 mmol) was combined with THF (10 ml) and dimethylsulfoxide (0.16 ml) to give an orange solution. Then ethyl propiolate (858 mg, 0.89 ml, 8.75 mmol), copper (I) iodide (556 mg, 2.92 mmol) and 2,6- lutidine (625 mg, 0.68 ml, 5.83 mmol) were added and the reaction mixture was stirred for 2 hours at room temperature. Water and ethyl acetate were added and the layers were separated. The organic layer was washed with 1 N hydrochloric acid and brine, dried over MgS04 and filtered. The filtrate was concentrated under vacuum to yield a brown solid, which was adsorbed on silica gel and purified by flash chromatography (20 g Silica gel, 20% ethyl acetate in heptane) yielding 698 mg (84%) of a light yellow solid. MS (ISP): 284.2 ([M+H]+).

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

Synthetic Route of 22236-10-8, A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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 p-toluenesulfonic acid monohydrate (9.25 g, 48.6 mmol) in acetonitrile (65 mL)4- (difluoromethyloxy) aniline (2.00 mL, 16.2 mmol) was added at room temperature.To the reaction solution was added dropwise a solution of sodium nitrite (2.24 g, 32.4 mmol) and potassium iodide (6.72 g, 40.5 mmol) in water (11 mL) at 10 C., and the mixture was stirred at room temperature for 3 hours did.Water was added to the reaction solution,And extracted with ethyl acetate.The combined organic layers were successively washed with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium thiosulfate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.The obtained crude product was purified by column chromatography (hexane) to obtain a pale pink oil (3.98 g, yield: 91%) of 1-difluoromethyloxy-4-iodobenzene.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; HOKKO CHEMICAL INDUSTRY COMPANY LIMITED; HANDA, MASAMI; MIZUTA, SATOSHI; HIRAI, KENJI; OKAMURA, DAIGO; GUSHIKAWA, TORU; (111 pag.)JP2015/848; (2015); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 22236-10-8, 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 22236-10-8 as follows.

A solution of 4-difiuoromethoxyaniline (258 mg, 1.62 mmol) and 4-difluoromethoxyphenyl isocyanate (300 mg, 1.62 mmol) in toluene (8.1 niL) is heated at 7O0C for 1.5 h. The resulting white solid is collected by suction filtration and dried with suction for 30 min to obtain N,N’-bis[4- (difluoromethoxy)phenyl]urea as a white solid. 1H NMR: (CD3OD) 7.45 (dd, 4H), 7.09 (dd, 4H), 6.91(dt, 2H, Ji = 56 Hz).

According to the analysis of related databases, 22236-10-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/49941; (2006); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 4-CHLORO-2-METHYL-QUINAZOLINE (450 mg, 2.52 mmol), 4- difluoromethoxy-phenylamine (0.32 ml, 2.52 mmol) and sodium acetate (248.07 mg, 3.02 mmol) in 6 mL of solvent (THF: water = 1 : 1) was stirred at 70 C for 1 h. The reaction mixture was diluted with 30 mL of ethyl acetate. It was washed with brine, dried over anhydrous NA2S04, filtered and concentrated. The crude product was purified by chromatography on silica gel with acetate and hexane (1: 5) as eluent, yielding 713 mg of title compound (94 %). H NMR (CDC13) : 7.87-7. 76 (m, 5H), 7.51 (t, J = 8.4 Hz, 1H)), 7.40 (brs, 1H), 7.19 (d, J = 8.7 Hz, 2H), 6.76-6. 27 (three single peaks, 1H), 2.71 (s, 3H).

The synthetic route of 4-(Difluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MYRIAD GENETICS, INC.; CYTOVIA, INC.; WO2005/3100; (2005); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Quality Control of 4-(Difluoromethoxy)aniline

Step A: 6-(Difluoromethoxy)benzo[d]thiazol-2-amine To 4-(difluoromethoxy)aniline (9.55 g, 60 mmol) in acetic acid (90 mL) was added potassium thiocyanate (KSCN) (12.41 mL, 240 mmol). The mixture was stirred for 20 minutes (KSCN dissolved into solution). To this mixture bromine (3.08 mL, 60.0 mmol) in acetic acid (40 mL) was added dropwise over 20 minutes. The reaction was stirred at room temperature overnight. It was poured into a mixture of 800 ml ice water and 200 ml saturated ammonium hydroxide. The product was extracted with ethyl acetate (5¡Á). The organics were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford 6-(difluoromethoxy)benzo[d]thiazol-2-amine (12.6 g, 52.4 mmol, 87% yield) as a yellow solid.

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; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem