Category: 261762-56-5

Related Products of 261762-56-5, 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 261762-56-5 as follows.

In a four-necked 250 mL round-bottomed flask, equipped with a thermometer, a reflux condenser with pressure equalizer, a dry ice cooled dropping funnel (-30 C) and a gas inlet, 50.0 g (purity 97.0 w%, 302 mmol, 1.0 eq) of l-chloro-2-fluoro-3-methoxy-benzene (1, CAS- No. 261762-56-5) were dissolved in 70 mL of chlorobenzene. To the solution 53.1 g (purity 98.0 w%, 332 mmol, 1.1 eq) bromine was added over one hour at 5-10 C internal temperature via cooling externally at 0 C. After complete addition the reaction was allowed to reach 25 C. The reaction was continued for further 8 hours under a constant stream of nitrogen purge gas to remove HBr from the reaction mixture. Afterwards a HPLC measurement indicated >98% conversion. The reaction solution was then washed with 100 mL of aqueous saturated NaHC03 solution and 50 mL of deionized water. Afterwards the organic phase was dried over MgSC^, the drying agent was filtered off and the solvent was removed in vacuum at 65 C and 5 mbar to leave 72.6 g (90%, purity 90%) of a brownish solid. The solid was purified via vacuum distillation at 10 mbar and temperature of 118-122 C to yield 57.4 g (79%, purity 99%) of a white solid. NMR (CDC13, 400 MHz) delta (ppm) = 7.34 (dd, J= 8.0, 2.0 Hz, 1H), 6.79 (dd, J= 8.0, 8.0 Hz, 1H), 3.89 (s, 3H).

According to the analysis of related databases, 261762-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; MUeHLTHAU, Friedrich, August; FORD, Mark, James; ERVER, Florian; BREMEYER, Nadine; PLATZEK, Johannes; GUIMOND, Nicolas; BADER, Thomas; ALBRECHT, Uwe; (129 pag.)WO2018/46684; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 261762-56-5, 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 261762-56-5 as follows.

Example 12 5-{[1-(4-Chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-(methoxymethyl)propyl]amino}-7-fluoro-1H-quinolin-2-one; (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 10 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After 1.5 hours at -70 1 g (6.9 mmol) N,N’-dimethoxy-N,N’-dimethyl urea in 6 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 7.5 ml of a 2 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel (ethyl acetate in hexane 0 to 30%) to yield 0.59 g 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid. 1H-NMR (CDCl3); delta=3.35 (br, 3H), 3.49 (br, 3H), 3.98 (s, 3H), 6.99 (dd, 1H), 7.13 (dd, 1H).0.44 ml (5.1 mmol) 1,1,1-trifluoro-2,3-epoxypropane in 7.5 ml THF and 2.2 ml hexane are cooled to -100 C. and 2.03 ml of a 2.5 M n-butyl lithium solution (5.1 mmol) in hexane are added over 15 minutes while the temperature does not exceed -95 C. 10 minutes after complete addition 0.57 g (2.3 mmol) 4-chloro-3-fluoro-2,N-dimethoxy-N-methylbenzamid in 10 ml THF are added over 15 minutes while the temperature does not exceed -95 C. After 3 hours at -100 C. 2.3 ml diethyl ether is added and the reaction mixture is warmed to room temperature over 14 hours. The reaction is quenched by addition of saturated ammonium chloride solution. The phases were separated and the aqueous layer is extracted twice with diethyl ether, the combined organic phases washed with brine, dried over sodium sulphate and then evaporated to yield 570 mg of (4-chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone. 1H-NMR (CDCl3); delta=2.99 (dq, 1H), 3.37 (d, 1H), 4.14 (d, 3H), 7.18 (m, 1H), 7.19 (m, 1H). 285 mg (0.95 mmol) (4-Chloro-3-fluoro-2-methoxyphenyl)[2-(trifluoromethyl)oxiranyl]methanone are stirred with 622 mg (1.9 mmol) caesium carbonate in 6.7 ml methanol. The reaction is quenched by addition of water after one day. The aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine, dried over sodium sulphate and then evaporated to yield 262 mg 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one. To 27 mg (0.15 mmol) 5-Amino-7-fluoro-1H-quinolin-2-one and 50 mg (0.15 mmol) 1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethypropan-1-one in 0.45 ml toluene and 0.13 ml 1,4-dioxane are added 33 mul acetic acid and 0.12 ml tetra butyl orthotitanate. The mixture is heated over 20 hours to 110 C., cooled to room temperature and poured into aqueous ammonium fluoride solution. Ethyl acetate is added and the mixture is stirred vigorously for 30 minutes. Phases are separated and two times extracted with ethyl acetate. The combined organic phases are concentrated to yield quantitatively 5-{[1-(4-chloro-3-fluoro-2-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-methoxymethylpropylidene]amino}-7-fluoro-1H-quinolin-2-one. The raw imine in 4.2 ml methanol is cooled to 5 C. and 120 mg sodium boron hydride are added in multiple portions over the period of 72 hours. The reaction is quenched by addition of saturated ammonium chloride solution and diluted with water and ethyl acetate. The phases are separated, the aqueous layer is extracted with ethyl acetate, the combined organic phases are washed with brine and dried over sodium sulphate. After removal of the solvent preparative thin layer chromatography on silica gel (acetone in methylene chloride, 30%) yields 9.5 mg of the title compound.1H-NMR (CD3OD); delta=3.44 (s, 3H), 3.65 (m, 1H), 3.69 (d, 1H), 4.05 (d, 3H), 5.44 (s, 1H), 6.03 (dd, 1H), 6.30 (dd, 1H), 6.45 (d, 1H), 7.12 (dd, 1H), 7.35 (dd, 1H), 7.94 (d, 1H).

According to the analysis of related databases, 261762-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, A new synthetic method of this compound is introduced below., Formula: C7H6ClFO

1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF was cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane were added. After one hour at -70 3.93 ml DMF in 7 ml THF were added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous hydrochloric acid were added and the reaction was warmed to ambient temperature over 18 hours. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

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; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; ASTRAZENECA AB; US2010/16338; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 261762-56-5, 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 3 5-{[1-(2-Chloro-3-fluoro-4-methoxyphenyl)-3,3,3-trifluoro-2-hydroxy-2-([methylsulfanyl]methyl)propyl]amino}-1H-quinolin-2-one2-Chloro-3-fluoro-4-methoxybenzaldehyde; 1 g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF are cooled to -70 C. and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane are added. After one hour at -70 3.93 ml DMF in 7 ml THF are added at -70 C. and the mixture is stirred another hour at -70 C. 15 ml of a 1 M aqueous HCl are added and the reaction is warmed to ambient temperature over 18 hours. The reaction mixture is partitioned between diethyl ether and water. The aqueous phase is extracted with diethyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and evaporated. The crude product is purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta=3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

The synthetic route of 1-Chloro-2-fluoro-3-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H6ClFO

To a 0 C solution of 1-chloro-2-fluoro-3-methoxybenzene (1.606 g, 10 mmol) in acetic acid (5.00 ml) was added fuming nitric acid (0.93 3 ml, 20.00 mmol) followed bythe dropwise addition of sulfuric acid (2.132 ml, 40.0 mmol). After 30 mm, the reaction mixture was poured into water and diluted with ethyl acetate. The organic phase was separated and washed 2x with saturated NaHCO3 followed by a final brine wash. The organic solution was then dried over Mg504, filtered, concentrated and purify by ISCO (120g, 10-50% EtOAc/Hexanes, 25 mm. Desired regioisomer eluted second) affordingIntermediate I-43A (1.lOg, 5.35 mmol, 53% yield) as a yellow solid. LC-MS: Method H,RT = 1.13 mm, MS (ESI) m/z: No Ionization Observed (M+H)t ?H NMR (400MHz, CHLOROFORM-d) oe 7.89 (dd, J=9.2, 2.2 Hz, 1H), 6.95 (dd, J=9.4, 7.6 Hz, 1H), 4.00 (s, 3H). Regiochemistry confirmed through NMR analysis of both regioisomeric products.

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; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, 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 261762-56-5, Quality Control of 1-Chloro-2-fluoro-3-methoxybenzene

Example 40 Preparation of 2-(4-chloro-3-fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dloxaborolane [0281] [0282] To a 100 mL flask charged with THF (25 mL) was added 1-chloro-2-fluoro-3-methoxybenzene (1 g, 6.23 mmol). The reaction flask was cooled to -78 C. in a dry ice acetone bath and n-butyllithium (0.399 g, 6.23 mmol) was added. After 40 min of stirring at -78 C. the reaction mixture was warmed to an internal temperature of -40 C. and the cooled to -78 C. in a dry ice acetone bath. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.159 g, 6.23 mmol) in THF (5 mL) was added in one portion. The dry ice/acetone bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was nuetralized with 1N HCl solution and diluted with Et2O (50 mL) and water. The resulting organic layer was dried over Na2SO4, filtered and concentrated to give 1:1 mixture of 2-(4-chloro-3-fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane and 2-(2-chloro-3-fluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as light yellow oil that was used in the next step without further purification (300 mg): ESIMS m/z 271 ([M+H]+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Chloro-2-fluoro-3-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 261762-56-5, These common heterocyclic compound, 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, 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.

2-Chloro-3-fluoro-4-methoxybenzaldehyde 1g (6.2 mmol) 3-Chloro-2-fluoroanisole in 20 ml THF was cooled to -70C and 2.7 ml of a 2.5 M n-butyl lithium solution in hexane were added. After one hour at -70 3.93 ml DMF in 7 ml THF were added at -70C and the mixture is stirred another hour at -70C. 15 ml of a 1 M aqueous hydrochloric acid were added and the reaction was warmed to ambient temperature over 18 hours. The reaction mixture was partitioned between diethyl ether and water. The aqueous phase was extracted with diethyl ether, the combined organic phases were washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel to yield 0.25 g 2-chloro-3-fluoro-4-methoxybenzaldehyde. 1H-NMR (CDCl3); delta = 3.98 (s, 3H), 6.98 (dd, 1H), 7.75 (dd, 1H), 10.30 (s, 1H).

The synthetic route of 261762-56-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; AstraZeneca AB; EP2149558; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 261762-56-5, 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 261762-56-5 as follows.

To a mixture of 1-chloro-2-fluoro-3-methoxy-benzene (5.00 g, 31.1 mmol) in dichloromethane (40 mL) was added titanium tetrachloride (10.0 g, 52.9 mmol) dropwise at 0 C under nitrogen. Dichloro(methoxy)methane (3.58 g, 31.1 mmol) was then added to the solution. Then the mixture was stirred at rt for 3 hours. On completion, the residue was poured into ice- water (50 mL) and extracted with ethyl acetate (50 mL). The combined organic layer was washed with brine (50 mL), dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with petroleum ether/ethyl acetate (20/1 to 3/1) to give the title compound. ?HNMR (400 IVIFIz, DMSO-d6) = 10.15 (s, 1H), 7.74 (d, J6.8 Hz, 1H), 7.37 (d, J 6.0 Hz, 1H), 3.98 (s, 3H).

According to the analysis of related databases, 261762-56-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (163 pag.)WO2017/156179; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics