Category: 367-22-6

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

To a solution of 1005 (10.0 g, 68.7 mrnol) in heptane (100 ml) was added(Boc)20 (16.4 rnL, 76.6 rnmol) After stirring the reaction mixture at 80C for 16 h, solvent wasevaporated and the residue was purified by Comhiflash column chromatography (hexane/EtOAc, 1:2) to afford 1006 (7.0 g, 43%) as a solid. 1H NMR (400 MHz, CDC13): oe 7.44 (dd, 1H), 727 (t, IH), 694 (dd, 1H), 6.53 (s, 1H). 1.50 (s, 9H).

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

Reference:
Patent; IOMET PHARMA LTD.; MERCK SHARP & DOHME CORP.; COWLEY, Phillip, M.; HAN, Yongxin; (67 pag.)WO2017/48612; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature 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.

Example; 4-tert-Butyl-N-(4-chloro-5-fluoro-2-iodo-phenyl)-benzenesulfonamide; Step 1:; Iodine (873 mg, 3.44 mmol) was added to a solution of 4-chloro-3-fluoroaniline (500 mg, 3.44 mmol) and potassium hydroxide (193 mg, 3.44 mmol) in N,N-dimethylformamide (?DMF?) (10 mL) and the reaction was stirred at 60 C. for 18 hours. The crude mixture was subsequently partitioned with ethyl acetate (20 mL) and saturated ammonium chloride (20 mL) and the layers separated. The organic layer was washed with saturated ammonium chloride (3¡Á20 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography (0-50% ethyl acetate in hexanes) to afford the desired iodoaniline (234 mg, 25%).

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:
Patent; CHEMOCENTRYX, INC.; US2009/5410; (2009); 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., COA of Formula: C6H5ClFN

Step 1 : tert-butyl (4-chloro-3-fluorophenyl)carbamate. To a solution of 4-chloro-3-fluoroaniline (7.50 g, 51.50 mmol) in DCM (150 mL) was added di-tert-butyl dicarbonate (11.96 mL, 51.5 mmol) dropwise. The reaction mixture was stirred at 25C for 16 h under N2 atmosphere (balloon). TLC showed a new spot and the SM was consumed. The mixture was diluted with water (200 mL) and extracted with EtOAc (150 mL x2). The combined organic layers were dried over Na2S04, filtered and the filtrate was concentrated. The residue was purified by flash silica gel chromatography (0-18% EtOAc/PE gradient) to afford the title compound.

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; MERCK SHARP & DOHME CORP.; MERTZ, Eric; EDMONDSON, Scott, D.; SO, Sung-Sau; SUN, Wanying; LIU, Weiguo; NEELAMKAVIL, Santhosh, F.; GAO, Ying-Duo; HRUZA, Alan; ZANG, Yi; ALI, Amjad; MAL, Rudrajit; HE, Jiafang; KUANG, Rongze; WU, Heping; OGAWA, Anthony, K.; NOLTING, Andrew, F.; (152 pag.)WO2016/168098; (2016); A1;,
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, Formula: C6H5ClFN

General procedure: A solution of the respective 1H-indazole-5-carboxylic acid or 1-alkyl-1H-indazole-5-carboxylic acid (1 or 7, 10, 1.0 mmol), 3,4-dichaloaniline or 5,6-dichloropyridin-3-amine (-5 or 6,1.1-1.2 mmol), N-ethyl-N-(3-dimethylaminopropyl)carbodiimidehydrochloride (EDC-HCl, 1.0-1.2 mmol) in methanol (5.0 mL) wasstirred over night at room temperature. The reaction was thenpoured into water (10 mL), stirred for 30 min at room temperature,filtered, washed with water (3 x 10 mL), and then dried at 70 C.The crude product was purified by column chromatography onsilica gel (mobile phase: dichloromethane/MeOH 9/1 v/v) following by recrystallization from petroleum ether/dichloromethane.

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; Tzvetkov, Nikolay T.; Stammler, Hans-Georg; Georgieva, Maya G.; Russo, Daniela; Faraone, Immacolata; Balacheva, Aneliya A.; Hristova, Silvia; Atanasov, Atanas G.; Milella, Luigi; Antonov, Liudmil; Gastreich, Marcus; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 404 – 422;,
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., Product Details of 367-22-6

Step 14: Preparation for N-(4-Chloro-3-fluorophenyl)-5-(tetrahydro-2H-pyran-4-yloxy)-2,3-dihydro-[1,4]dioxino[2,3-f]-quinazolin-10-amine To a solution of 10-Chloro-5-(tetrahydro-2H-pyran-4-yloxy)-2,3-dihydro-[1,4]dioxino[2,3-f]quinazoline (0.1 g, 0.3 mmol) in isopropanol (3 mL) was added 4-chloro-3-fluoroaniline (0.06 g, 0.4 mmol). The solution was stirred at 80 C. for 4 hours. After cooling to ambient temperature, the solution was concentrated to obtain a yellow solid which was purified by column chromatography on silicon gel (dichloromethane:methanol=100:1) to obtain a yellow solid (0.07 g, yield=49%). 1H NMR (DMSO-d6, 400 MHz): 10.51 (s, 1H), 8.75 (s, 1H), 7.95-7.92 (m, 1H), 7.65-7.64 (m, 1H), 7.54 (t, 1H, J=8.9 Hz), 7.30 (s, 1H), 4.77 (dd, 1H, J=4.4 Hz), 4.61 (br, 2H), 4.60 (br, 2H), 3.92-3.89 (m, 2H), 3.56-3.50 (m, 2H), 2.10-2.07 (m, 2H), 1.72-1.69 (m, 2H); MS: 432(M+H+).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 367-22-6.

Reference:
Patent; BEIJING SCITECH-MQ PHARMACEUTICALS LIMITED; SHENG, Wang; YANG, Leifu; PAN, Zhiyong; (46 pag.)US2017/355683; (2017); A1;,
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., SDS of cas: 367-22-6

4-chloro-3-fluoroaniline (2g, 13.7 mmol) was dissolved in 60 mL of dichloromethane. Under ice bath, saturated sodium bicarbonate solution (60 mL) was added. The mixture was stirred at 0 C and triphosgene (1.36g, 4.58 mmol) was added. The mixture was stirred at 0 C for 1 hr and then extracted with dichloromethane and water. The organic layer was dried with sodium sulfate and filtered. The filtrate solution was concentrated and the residue was treated with 50 mL of hexanes. The hexane solution was concentrated to remove all solvents. The residue was dissolved in 12 mL of hexanes and filtered. The solution was concentrated and dried to give l-chloro-2-fluoro-4-isocyanatobenzene as an off white solid (1.69 g). 1H NMR (400 MHz, CHLOROFORM- )? ppm 6.82 – 6.90 (m, 1 H) 6.93 (dd, 7=9.22, 2.65 Hz, 1 H) 7.31 – 7.41 (m, 1 H).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BROTHERTON-PLEISS, Christine E.; CHEN, Zhi; ERICKSON, Shawn David; KIM, Kyungjin; LI, Hongju; LOVEY, Allen John; QIAN, Yimin; SO, Sung-Sau; WOVKULICH, Peter Michael; YI, Lin; WO2014/60341; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. COA of Formula: C6H5ClFN

A solution of methyl 4-nitro-3-(1-piperidinylmethyl)benzoate (16.05 g, 57.7 mmol) in Tetrahydrofuran (THF) (100 mL) and methanol (100 mL) was treated with LiCH (250 mL, 250 mmol) and stirred at ambient temperature for 4 hours. The mixture was concentrated togive crude 4-nitro- 3-(1-piperidinylmethyl)benzoic acid (20.51 g). The acid intermediate was suspended in SOd2 (50 mL, 685 mmol), refluxed for 1 .5 hours, and concentrated to give 4- nitro-3-(1-piperidinylmethyl)benzoyl chloride (LCMS in meoh, ES+279, methyl ester). The acyl chloride was suspended in dichloromethane (DCM) (100 mL), treated with 4-chloro-3- fluoroaniline (7.97 g, 54.8 mmol), Et3N (12.06 mL, 87 mmol), and stirred at ambienttemperature overnight. Additional Et3N (4 mL), DCM (11 mL), and aniline (418 mg) was added, and the reaction was stirred overnight. The suspension was quenched with sat. NaHCO3, extracted with DCM 2x, washed with sat. NaHCO3 lx, Brine, dried with Na2SO4, filtered, and concentrated. Purification by silica gel column chromatography (0-50% EtOAc/Hexane) gave N-(4-chloro-3-fluorophenyl)-4-nitro-3-(1-piperidinylmethyl)benzamide (13.86 g, 35.4 mmol, 61.3 % yield) as yellow solid. LC/MS (m/z) ES+ = 279.3 (M+1)+

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; JEFFREY, Jerry; TANG, Jun; TAI, Vincent Wing-Fai; TEMELKOFF, David; VELTHUISEN, Emile Johann; WEATHERHEAD, Jason Gordon; (101 pag.)WO2018/2902; (2018); 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., Recommanded Product: 367-22-6

To 4-chloro-3-fluoroaniline (25g, 0.17 mmol) in 250 mL of H2O was added NaHCO3 (21.6g, 0.25 mmol). After cooling to 0 C, iodine (43.5g, 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 (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A.MS (ESI) m z: 145.2 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 367-22-6.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56034; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 367-22-6, 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.

4-Chloro-3-fluoro-phenylamine (10 g, 68.7 mmol) was dissolved in dichloromethane (38 ml) and treated with sodium bicarbonate (6.82g, 72.1 mmol) in water (100 ml). At rt methyl chloroformate (8 ml, 103.0 mmol) was added dropwise over a period of 25 min (temperature raises from 22 to 28 C.). After 1.5 h stirring at rt, the reaction mixture was diluted with dichloromethane (100 ml). After separation, the organic phase was washed with sat. aq. NaCl solution (45 ml), dried over magnesium sulfate, filtered and diluted with hexane (140ml). The dichloromethane was then removed under vacuo and the resulting suspension filtered leading to (4-chloro-3-fluoro-phenyl)-carbamic acid methyl ester (13g, 92%) as a white powder. MS (EI) 203.1 (M)+.

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

Reference:
Patent; Conte, Aurelia; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Mueller, Werner; Pflieger, Philippe; US2007/185182; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 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.

Intermediate 45-Amino-N-(4-ch[oro-3-f[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide A mixture of 5-amino-3-methy[-1 ,2-thiazo[e-4-carboxy[ic acid [CAS-RN: 22131 -51 -7,for the synthesis, p[ease see: J. Goerde[er, H. Horn, Chem. Ber. (1963), 96, 1551-1560.] (5.00 g, 9.93 mmo[, 1.0 eq) and thiony[ ch[oride (20.7 mL, 284 mmo[,9.0 eq) was stirred at 80 C for 2 h. After coo[ing, the vo[ati[e components were removed in vacuo. The crude acid ch[oride was di[uted with to[uene and concentrated at the rotary evaporator. This process was repeated one more time.The acid ch[oride (1.75 g, 9.93 mmo[, 1.0 eq) observed this way was disso[ved in THF (15 mL). Then, 4-ch[oro-3-f[uoroani[ine [CAS-RN: 367-22-6] (2.89 mL, 19.9 mmo[, 2.0 eq) and triethy[ amine (2.01 mL, 19.9 mmo[, 2.0 eq) was added. The reaction mixture was stirred at rt overnight. After addition of water the crude reaction mixture was acidified with 1M hydroch[oric acid and extracted with EtOAc.The organic phase was washed with brine and dried with sodium su[fate. After remova[ of the vo[ati[e components the product was crysta[[ized from dich[oromethane and methano[. The precipitate was iso[ated by fi[tration and dried under high vacuum to give the tit[e compound (600 mg, 21% yie[d of theory based on the intermediate acid ch[oride).UPLC-MS (Method 2): Rt = 1.06 mm; MS (Elneg) m/z = 284 [M-H].1HNMR (400 MHz, DMSO-d6): oe [ppm] = 2.36 (s, 3H), 7.28 (s br, 2H), 7.41 (dd, 1H),7.51 (t, 1H), 7.81 (dd, 1H), 9.82 (s, 1H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics