Category: 367-22-6

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. 367-22-6, name is 4-Chloro-3-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 367-22-6

To 4-chloro-3-fluoroaniline (25g, 0.17 mmol) in 250 mL of H20 was added NaHC03 (21.6g, 0.25 mmol). After cooling to 0 C, iodine (43.5 g, 0.17 mmol) was added. After 18 h at rt, an additional 10.8 g of iodine was added and the reaction was stirred overnight. The reaction was extracted with DCM (4×250 mL), the combined organics were washed with sodium thiosulfate solution (2×250 mL) and brine (2×250 mL) and dried ( a2S04). Purification by silica gel chromatography gave 47 g of Intermediate 5A.MS (ESI) m/z: 145.2 (M+H)+.

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; CORTE, James R.; WO2013/55984; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H5ClFN

Compound 102[00318] 4-Chloro-3-fluoroaniline; (250.3g, 1.719mol) was added to a 5L four-neck round bottom flask equipped with overhead stirrer, reflux condenser, heating mantle, temperature controller, an internal temperature probe and an argon inlet. r°-Heptane (2000ml) and di-t- butyl-dicarbonate (450.3g, 2.064mol) were charged to the flask. The mixture was stirred under argon at room temperature for 15min allowing dissolution of the majority of the solids. The mixture was heated to reflux for 4h under argon (care: generation of CO2 g). Analysis of the reaction mixture by HPLC method Test 20 (THFrMeCN 1 :1) indicated complete conversion of starting material (Rt 4.57min) to one product (Rt 6.17min). [00319] The reaction was allowed to cool to 50-550C and transferred in two portions to a 3 L one-neck RBF. A total of 1500ml of distillate was removed by concentration in vacuo at 450C to give a peach colored solution with white crystals. The slurry was allowed to cool to room temperature, whilst stirring, for 1.5h. The flask was stored at 40C for 15h after which time the crystals were filtered under vacuum and washed with cold «-heptane (400ml). [00320] After drying at 350C under vacuum for 7h, very fine, white crystals of Compound 102 (393.1g, 93% yield) were obtained. Compound 102: C?Hi3ClFNO2 245.68gmol”. HPLC analysis (Test 20, MeCN): R1 6.16min; 99% purity (at) 254nm. m.p.: 103-1040C. 1H NMR OH (400 MHz, CDCl3): 1.51 (9H, s, 3 x CH3), 6.56 (IH, br-s, N-H), 6.94, 7.25, 7.35 (3 x 1Eta, 3 x m, 3 x Ar-H).

According to the analysis of related databases, 367-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; WO2008/42240; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 367-22-6, name is 4-Chloro-3-fluoroaniline, belongs to chlorides-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 367-22-6, category: chlorides-buliding-blocks

Step B: 4-Chloro-5-fluoro-2-iodo-phenylamine Iodine chloride (20.6 ml, 1M solution in DCM, 20.6 mmol) was added dropwise to a solution of 4-chloro-3-fluoroaniline (2 g, 13.7 mmol) in methanol (35 ml) at 0 C. and the reaction mixture was stirred for 1 h at room temperature. Volatiles were removed under reduced pressure, water was added and the mixture was extracted with dichloromethane. The combined organic layers were washed with water, dried with Na2SO4 and evaporated. The remaining residue was purified by chromatography with three consecutive columns (silica gel, heptane/EtOAc 98:2-93:7 and twice heptane/EtOAc 98:2-95:5) to obtain the title compound (2.51 g, 67%) as dark red solid. MS (ESI): 272.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-3-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Hoffmann-La Roche Inc.; Ceccarelli, Simona M.; Conte, Aurelia; Kuehne, Holger; Kuhn, Bernd; Neidhart, Werner; Obst Sander, Ulrike; Rudolph, Markus; US2013/116234; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 367-22-6, 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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The intermediate 4-ethoxy-1,3-benzenedisulfo chloride(1.2 g, 3.7 mmol) was dropwise added to a solution of 2,4-difluoro aniline (1.0 g, 7.5 mmol) with dichloromethane (15 mL) as solvent at room temperature under magneticstirring. After 10 min, triethylamine (0.5 mL) as acidbindingagent was dropwise added to the reaction mixture.The mixture was stirred under reflux at 35 C for about8 h. After the reaction completed as monitored by TLC, thesolvent was removed under reduced pressure. Under thecondition of ice bath, the mixture was dissolved in cold 5%NaOH aqueous solution to obtain filtrate. The solid wasobtained by adjusting the pH of filtrate with hydrochloricacid (VHCl: Vwater = 1:1) in the condition of ice salt bath.After filtrating and drying, crude product was prepared. Thecrude product was purified by recrystallization from ethanolwith excellent yield (Scheme 1).

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Xin; Liu, Xiujie; Qiu, kai; Xu, Xiang; Li, Caiwen; Wang, Yan; Medicinal Chemistry Research; vol. 28; 9; (2019); p. 1388 – 1401;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H5ClFN

N-(4-Chloro-3-fluorophenyl)-4-nitropyridin-3-amine NaH (422 mg, 60% dispersion in mineral oil, 10.6 mmol) was suspended in THF (20 mL) and 4-chloro-3-fluoroaniline (1.54 g, 10.6 mmol) and 3-fluoro-4-nitropyridine (500 mg, 3.52 mmol) were added. The reaction mixture was stirred for 18 h, quenched with sat aq NH4Cl (2 mL), and concentrated in vacuo. The residue was partitioned between water (50 mL) and DCM (50 mL) and the organic fraction was dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (207 mg, 22.0%) as an orange solid. LCMS (ES+): 268.0 [MH]+.

According to the analysis of related databases, 367-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Proximagen Limited; Espensen, Max; Patient, Lee; Evans, David; Savory, Edward; Simpson, Iain; US2014/275040; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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.

[0216] Ethyl 2-(4-chloro-3-fluorophenylamino)-2-oxoacetate (2′). TEA (2.28g, 0.023 mol) was added at once to a solution of 3 g (0.0206 mol) 4-chloro-3-fluoroaniline in 50 ml of DCM and then ethyl 2-chloro-2-oxoacetate (2.81 g, 0.0206 mol) was added dropwise at 0C. Reaction mixture was stirred at 0C for 1 h and then continued at room temperature (RT) for 6 h. The mixture was washed with 25% aqueous solution of K2C03 (2×50 ml) and water (50 ml). The product was dried over Na2S04 and evaporated. The residue was washed with ether and dried on the air to give ethyl 2-(4-chloro-3-fluorophenylamino)-2- oxoacetate (2′) (3.97 g, 78.6%) as a white powder; LC-MS (APCI+) m/z: calcd for C10H9CIFNO3: 245.03; found: 245 (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 4-Chloro-3-fluoroaniline, its application will become more common.

Reference:
Patent; NEW YORK BLOOD CENTER, INC.; THE UNITED STATES OF AMERICA as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES (WASHINGTON, DC); DEBNATH, Asim, Kumar; CURRELI, Francesca; KWONG, Peter, D.; KWONG, Young, Do; WO2013/36676; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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. name: 4-Chloro-3-fluoroaniline

General procedure: To a solution of compound 12 (bakuchiol-o-triflate) (1 mmol) in toluene (10 mL M), amine (3.0 mmol), Cs2CO3 (4.0 mmol), ligand (±) BINAP (0.6 mol) and Pd(OAc)2 (0.2 mol) were added under an inert atmosphere. The reaction mixture was degassed at RT and refluxed (120 C) for 24 hr. Then, the reaction mixture was brought to RT, diluted with EtOAc and filtered through celite. To the reaction mixture, brine (20 mL) was added and extracted with EtOAc (2 × 10 mL). The combined organic layerwas dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the product after silicagel chromatography purification (Hex/EtOAc, 9.5:0.5).

The synthetic route of 4-Chloro-3-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gautam, Lekh Nath; Ling, Taotao; Lang, Walter; Rivas, Fatima; European Journal of Medicinal Chemistry; vol. 113; (2016); p. 75 – 80;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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. COA of Formula: C6H5ClFN

Description 45 (78 mg, 0.37 mmol) and 3-fluoro-4-chloroaniline (54 mg, 0.37 mmol) inMeCN (2 ml) in the presence of a catalytic quantityof DMAP were stirred at 45 C for 16 h. The reaction was cooled and the resultant solid collected by filtration and rinsed with ether. Without further purification this solid was added to sodium hydroxide solution(1 % aqueous w/w, 2 ml) and heated at 80 OC for 30 min. The reaction was cooled, filtered throughCeliteX to remove insoluble impurities and the filtrate was acidified to pH-6 by the dropwise addition of hydrochloric acid (5N) to precipitate the product. The solid was collected by filtration, rinsed with water then ether and dried to give the title compound (70 mg). 1H NMR (400 MHz, DMSO)8 7.86(1H, s), 7.70(1H, t, J8.4), 7.43(1H, dd,J2. 2,10. 0), 7.14-7. 12(1H, m),3. 77 (3H, s) ;Mlz (ES+) 313,311 (M+H+).

The synthetic route of 4-Chloro-3-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; HOLLINGWORTH, Gregory, John; JONES, A., Brian; SPAREY, Timothy, Jason; WO2005/49613; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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: Compound 7 (488.2 mg, 2.0 mmol), 3,4-dimethoxybenzenamine 8a (367.6 mg, 2.4 mmol), and p-toluenesulfonic acid monohydrate (304.4 mg, 1.6 mmol) were dissolved in n-butanol (20 mL), then refluxed at 130 oC for 12 h. The resulting solution was neutralized with saturated NaHCO3 (5 mL). The mixture was extracted with ethyl acetate (50 mL×3). The organic layer was combined, dried over anhydrous Na2SO4, concentrated. The crude product was purified by silica gel chromatography to afford 9a (319.7 mg, 44.3% yield).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Long, Liang; Luo, Yu; Hou, Zhi-Jie; Ma, Hua-Juan; Long, Zi-Jie; Tu, Zheng-Chao; Huang, Lin-Jie; Liu, Quentin; Lu, Gui; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 805 – 812;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 367-22-6, name is 4-Chloro-3-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5ClFN

To a solution of 4-chloro-3-fluoroaniline (15 g, 103.05 mmol) in dichloromethane (150 mL) was added ICl (25 g, 154.57 mmol) drop wise. The resulting black mixture was stirred at 24-29C for 2h. The mixture was diluted with 100 mL dichloromethane and washed with saturated solution of sodium bicarbonate (200 mL). The organic layer was concentrated to give the crude residue, which was purified by flash column chromatography on silica gel (0 to 0.5%ethyl acetate in Petroleum ether) to afford compound 41a (8 g brown solid and 12 g black solid, 71.5% yield in total). LCMS: R t = 0.974 min in 5-95AB_220&254 chromatography (MERCK RP18 2.5-2mm), MS (ESI) m/z = 271.8 [M+H] +. 1H NMR: (400MHz, CDCl 3) delta 7.53 (d, J = 8.0 Hz, 1H), 6.46 (d, J = 10.4 Hz, 1H), 4.12 (s, 2H).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD; LI, Zhengtao; ZOU, Hao; ZHU, Wei; SHEN, Changmao; WANG, Rumin; LIU, Wengeng; CHEN, Xiang; TSUI, Honchung; YANG, Zhenfan; ZHANG, Xiaolin; (307 pag.)WO2019/149164; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics