Category: 367-22-6

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.

To a suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (24.5 g, 125 mmol) in Et20 (300 ml) at -10 C under N2 was added TFAA (12.23 ml, 88 mmol) dropwise. The mixture was allowed to warm to rt for 18 h. The reaction mixturewas diluted with hexane (300 ml), and filtered. The filtrate was washed with ice-water,10% aq NaHCO3, and brine, dried over Na2SO4, and concentrated. A pale yellow solid obtained as N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96 % yield). MS (ESI) m/z: 242.1 (M+H)t

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; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; PINTO, Donald J. P.; CORTE, James R.; EWING, William R.; (163 pag.)WO2016/205482; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products 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.

Step C(2S)(M)-[7-[(4-c loro-3-fluorop enyl)amino]-4-(8-fluoro-5-m2-methyl-1 -oxo-1 ,2-dihyd -3-isoquinolinyl][( 1, 1-dimethylethyl)oxy]ethanoic acid[00186] A degassed mixture of (S)(M)-me y 2-(7-bromo-4-(8-fluoro-5-methylchroman-6- yl)-2-methyl-1-oxo-1 ,2-dihydroisoquinolin-3-yl)-2-(tert-butoxy)acetate (22.00 mg, 0.040 mmol), 4-chloro-3-fluoroaniline (1 1.72 mg, 0.081 mmol) and sodium tert-butoxide (1 1 .61 mg, 0.121 mmol) in 1 ,4-Dioxane (1.0 mL) was treated with Pd2(dba)3 (2.084 mg, 2.013 muetaetaomicronIota) and 2- dicyclohexylphosphino-2′-(N,N-dimethyl-amino)biphenyl (3.17 mg, 8.05 mumol) and then irradiated in the microwave at 100 C for 10 minutes. The mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate, followed by brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude residue in methanol (1 .0 mL), tetrahydrofuran (THF) (1 .0 mL) and water (0.2 mL) was treated with lithium hydroxide (19.28 mg, 0.805 mmol) and then heated at 65 C for 4 hours. The mixture was concentrated, water was added and the mixture was adjusted to pH 3 with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate and the extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase chromatography to afford the title compound as a tan solid (1 1.8 mg, 49%). 1H NMR (400MHz ,CHLOROFORM-d) delta = 8.10 (m, 1 H), 7.32 – 7.17 (m, 2 H), 6.93 (m, 1 H), 6.89 – 6.74 (m, 3 H), 5.18 (s, 1 H), 4.31 (m, 2 H), 3.71 (s, 3 H), 2.78 – 2.67 (m, 2 H), 2.15 (m, 2 H), 1 .96 (s, 3 H), 1.23 (s, 9 H); LC/MS (m/z) ES+ = 598 (M+1 ).

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; GLAXOSMITHKLINE LLC; DE LA ROSA, Martha Alicia; HAYDAR, Simon, N.; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WO2012/102985; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference 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: A solution of the corresponding 1H-indazole-5-carbaldehyde(2), 1-methyl-1H-indazole-5-carbaldehyde (9) or 1-(2-methoxyethyl)-1H-indazole-5-carbaldehyde (10) (1.0 equiv.),different substituted anilines 3e6 (1.1 equiv.) and acetic acid(0.1 mL/mmol, pH 4e5) in ethanol (3.0 mL/mmol) was stirred underreflux until a precipitation took place. After cooling to roomtemperature, the reaction mixture was sonificated until completeprecipitation. The precipitate formed was filtered and dried at70 C. The crude product was purified by column chromatographyon silica gel (mobile phase: dichloromethane/MeOH 9/1 v/v) andrecrystallized three times from petroleum ether/dichloromethane.

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

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

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 367-22-6 as follows. Recommanded Product: 4-Chloro-3-fluoroaniline

Into a 500-mL round-bottom flask was placed 4-chloro-3-fluoroaniline (5.08 g, 34.9 mmol), ACN (200 mL), and NBS (18.69 g, 105.0 mmol). The resulting solution was stirred for 12 h at RT and then was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with a gradient of ethyl acetate/petroleum ether (1 :200 to 1 : 100). This resulted in 9.7 g (92%) of the title compound as a light yellow solid. MS-ESI: 303.8/305.8/301.8 (M+l).

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; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); 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., SDS of cas: 367-22-6

Step 12: Preparation for N-(4-Chloro-3-fluorophenyl)-5-(tetrahydrofuran-3-yloxy)-2,3-dihydro-[1,4]dioxino[2,3-f]quinazolin-10-amine To a solution of 10-chloro-5-(tetrahydrofuran-3-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-flouroaniline (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 (0.09 g, yield=62%). 1H NMR (DMSO-d6, 400 MHz): delta 10.45 (s, 1H), 8.73 (s, 1H), 7.97-7.94 (m, 1H), 7.66-7.65 (m, 1H), 7.54 (t, 1H, J=8.9 Hz), 7.14 (s, 1H), 5.20-5.18 (m, 1H), 4.61-4.59 (m, 2H), 4.45-4.44 (m, 2H), 3.96-3.88 (m, 3H), 3.81-3.79 (m, 1H), 2.37-2.34 (m, 1H), 2.08-2.06 (m, 1H). MS: 418(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

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, SDS of cas: 367-22-6

General procedure: To a stirred solution of anilines (3.29 mmol) in dichloromethane (6 mL) was added triethylamine (9.89 mmol) at room temperature and stirred at room temperature for 10 min and added aryl chloro formate (4.93 mmol) at 0 C and stirred at room temperature for 2 h. The reaction mixture was concentrated under reduced pressure and the crude material washed with 10 % diethyl ether in pentane to afford the pure compounds. Without further purification used for next step. Yields of the products varied between 65 to 85 %.

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:
Article; Bhasker, G Vijaya; Satyanarayana; Latha; Laxminarayana; Chary, M Thirumala; Asian Journal of Chemistry; vol. 30; 4; (2018); p. 771 – 774;,
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. Application In Synthesis of 4-Chloro-3-fluoroaniline

A mixture of 5-amino-3-methyl-1 ,2-thiazole-4-carboxylic acid [CAS-RN: 22131 -51-7, for the synthesis, please see: J. Goerdeler, H. Horn, Chem. Ber. (1963),96, 1551-1560.] (5.00 g, 9.93 mmol, 1.0 eq) and thionyl chloride (20.7 mL,284 mmol, 9.0 eq) was stirred at 80 C for 2 h. After cooling, the volatilecomponents were removed in vacuo. The crude acid chloride was diluted with toluene and concentrated at the rotary evaporator. This process was repeated one more time. The acid chloride (1.75 g, 9.93 mmol, 1.0 eq) observed this way was dissolved in THF (15 mL). Then, 4-chloro-3-fluoroaniline [CAS-RN: 367-22-6] (2.89 mL, 19.9 mmol, 2.0 eq) and triethyl amine (2.01 mL, 19.9 mmol, 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 hydrochloric acid and extracted with EtOAc. The organic phase was washed with brine and dried with sodium sulfate. After removal of the volatile components the product was crystallized from dichloromethane and methanol. The precipitate was isolated by filtration and dried under high vacuum to give the title compound (600 mg,-21% yield of theory based on the intermediate acid chloride).UPLC-MS (Method 2): Rt = 1.06 mm; MS (Elneg) m/z = 284 [M-H].1H-NMR (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 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 367-22-6, 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. 367-22-6 name is 4-Chloro-3-fluoroaniline, 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.

At 0 C, to a mixture of 4-chloro-3-fluoroaniline (7 g, 48.1 mmol) in DCM (100 mL) was added pyridine (7.8 mL, 96 mmol), followed by phenyl carbonochloridate (6.3 mL, 50.5 mmol). The mixture was stirred at 0 C for 1 h, then warmed up to rt overnight. The mixture was washed with IN HCl and back extracted with DCM. The combined organics were washed with brine, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give phenyl (4-chloro-3-fluorophenyl)carbamate (12 g, 45.2 mmol, 94 % yield) as a colorless solid. The crude product was used without further purification.LC/MS (ESI): m/z 266.1 (M+H)+, 1.13 min (ret. time).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BAILEY, James; CHEN, Yao; HURLE, Mark; LEACH, Craig; TURUNEN, Brandon; (103 pag.)WO2018/134731; (2018); 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. HPLC of Formula: C6H5ClFN

To a solution of 6-acetoxy-7-methoxy-quinazolin4-one (RO0505111-000) (1.0 g, 4.26 mmol) (from Example 15, Step A, supra) in SOCl2 (12.5 mL) (Aldrich) were added a few drops of DMF (0.1 mL). The reaction mixture was then heated with stirring at 100 C. for 3 hours. The solvents were evaporated and the residue was dried in vacuo. The residue was dissolved in 2-propanol (20 mL), followed by addition of 4-chloro-3-fluoroaniline (0.682 g, 4.69 mmol) (Aldrich). The reaction mixture was heated at 110 C. for 3 hours. The reaction mixture was cooled to room temperature and filtered. The precipitate was collected and dried in vacuo to give 6-acetoxy-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazoline as a gray solid. (Yield 1.54 g, 100%).

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

Reference:
Patent; Luk, Kin-Chun; Zhang, Zhuming; US2004/254205; (2004); 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., Product Details of 367-22-6

To a stirred solution of 20 g (137.4 mmol) 4-Chloro-3-fluoro aniline in 120 ml DCM was added 22.1 ml (274.8 mmol, 2 eq.) pyridine in one portion. The resulting solution was cooled to 0-3C in an ice bath, then a solution of 19.6 ml (151.2 mmol, 1.1 eq.) benzosulfochloride in 80 ml DCM was added dropwise within 1 h, whereas the temperature was kept between 0 and 3C. A color change from brownish over yellow and orange towards red was observed. After 1.5 h 120 ml water was added to the reaction mixture, the organic phase was washed with 120 ml water, and the aq. phase was washed twice with total 100 ml DCM. The combined organic phases were dried over Na2SO4, filtered with suction on a funnel with a fritted disk and washed with total 100 ml DCM. The solvent was carefully removed under reduced pressure, then 200 ml hexane was added. The total volume was reduced to 100 ml, whereupon the formation of a precipitate was observed. The suspension was stirred over night at 4C, the beige precipitate was filtered off with suction on a funnel with a fritted disk, washed with a total amount of 50 ml hexane and dried at 50C in vacuo for 3 h to yield 39.27 g (98.3% of theory) of the title compound as a beige solid (m.p = 114.9-116.1C). 1H-NMR data (CDCl3, 400 MHz): delta 7.82 (m, 2H), 7.60 (m, 1H), 7.48 (m, 2H), 7.24 (dd, 1H), 7.01 (dd, 2H), 6.78 (ddd, 1H). MS m/e (%): 284 ([M-H]+, 100). EA for C12H9ClFNO2S calc.: C 50.44, H 3.17, N 4.90 O 11.20. Found: C 50.46, H 3.21, N 4.92 O 11.28.

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; EP2011783; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics