Category: 367-22-6

Related Products of 367-22-6, A common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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 cooled (-10 C) suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (13.21 g, 125 mmol) in Et20 (300 mL) was added dropwise TFAA (12.23 mL, 88 mmol). The mixture was allowed to warm to rt overnight. The mixture was diluted with hexane (300 mL) and filtered. The filtrate was washed with ice water, 10%aq NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated to give N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96% yield), as a pale, yellow solid. MS(ESI) m/z: 242.1 (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; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); 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

Step 12: Preparation for N-(3-Chloro-4-fluorophenyl)-5-(1-methoxypropan-2-yloxy)-2,3-dihydro-[1,4]dioxino[2,3-f]quinazolin-10-amine To a solution of 10-Chloro-5-(1-methoxypropan-2-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 (0.09 g, yield=62%). 1H NMR (DMSO-d6, 400 MHz): delta 10.52 (s, 1H), 8.75 (s, 1H), 7.95-7.92 (m, 1H), 7.66-7.63 (m, 1H), 7.54 (t, 1H, J=8.9 Hz), 7.21 (s, 1H), 4.83-4.78 (m, 1H), 4.60 (br, 2H), 4.45 (br, 2H), 3.60-3.58 (m, 2H), 3.31 (s, 3H), 1.33 (d, 3H, J=6.4 Hz); MS: 420(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; BEIJING SCITECH-MQ PHARMACEUTICALS LIMITED; SHENG, Wang; YANG, Leifu; PAN, Zhiyong; (46 pag.)US2017/355683; (2017); 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.

Reference Example 152 1,1-dimethylethyl(4-chloro-3-fluorophenyl)carbamate A solution of 4-chloro-3-fluoroaniline (9.90 g, 68.0 mmol) and bis(1,1-dimethylethyl)dicarbonate (16.3 g, 74.8 mmol) in THF (100 mL) was stirred with heating at 60 C. for 15 hrs. Bis(1,1-dimethylethyl) bicarbonate (4.75 g, 21.8 mmol) was added again, and the mixture was further stirred at 60 C. for 3 days. The reaction mixture was concentrated under reduced pressure and crystallized from hexane to give the title compound as a white powder (11.8 g, 71%). 1H-NMR (300 MHz, DMSO-d6) delta: 1.48 (9H, s), 7.24 (1H, ddd, J=8.9, 2.4, 0.9 Hz), 7.45 (1H, t, J=8.8 Hz), 7.56 (1H, dd, J=12.2, 2.3 Hz), 9.73 (1H, s).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); 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, Computed Properties of C6H5ClFN

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 (43.5 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 (Na2SO4). Purification by silica gel chromatography gave 47 g of Intermediate 5A. MS (ESI) m/z: 145.2 (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-Chloro-3-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J.P.; SMITH II, Leon M.; SRIVASTAVA, Shefali; WO2013/56060; (2013); 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., Safety of 4-Chloro-3-fluoroaniline

Into a 500-mL round-bottom flask, was placed 4-chloro-3-fluorobenzenamine (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 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+1).

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; IFM THERAPEUTICS, INC; GLICK, Gary; GHOSH, Shomir; ROUSH, William R.; (328 pag.)WO2017/184624; (2017); 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.

A. 4-Chloro-3-fluorobenzenesulfonyl chloride The title compound was prepared using the method of Organic Syntheses Vol. 60, 121-124. A solution of 4-chloro-3-fluoro aniline (5 g, 0.034 mol) in glacial HOAc (10 mL) was added slowly to concentrated HCl (30 mL) to form a white precipitate. The mixture was cooled in a dry ice-ethanol bath. A solution of NaNO2 (3.08 g, 0.045 mol) in H2O (5 mL) was added dropwise while stirring with a glass rod, maintaining the temperature at or below -5 C. The mixture was stirred intermittently while in the bath for 1 h. In a separate flask, HOAc (40 mL) was saturated with SO2 using a gas dispersion tube (about 15 min). To this acetic acid solution was added cuprous chloride (0.68 g, 7 mmol), which gave a grey solution. The SO2 was bubbled through until the solution turned green-blue. The solution was cooled in a dry ice-ethanol bath and the diazonium salt mixture was added in portions while stirring with a glass rod. After the addition was complete, the reaction was removed from the bath and allowed to come to 0 C. over 15 to 20 min. with occasional stirring. The reaction was poured onto ice (100 mL) and extracted with CH2Cl2 (2*100 mL). The combined organic layer was washed with saturated NaHCO3 (3*40 mL), dried (Na2SO4), filtered and concentrated to afford a golden oil. The crude product was purified by silica gel column chromatography, eluding with a gradient of 10% to 15% CH2Cl2/hexanes to afford the title compound (5.5 g, 70%) as a golden oil. Mass Spectrum (-ESI): 209 [M-Cl+O]-.

Statistics shows that 4-Chloro-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 367-22-6.

Reference:
Patent; Wyeth; US2007/249722; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics