Category: 2267-25-6

Some common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, molecular formula is C7H6ClFO, 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. Product Details of 2267-25-6

Sodium hydride (60% dispersion in mineral oil, 31 mg, 0.776mmol) was added to an ice- cooled solution of the product of preparation 20 (135mg, 0.388mmol) in N1N- dimethylformamide (4mL) and the mixture was stirred at O0C for 15 minutes. 2-chloro-4-fluoro- anisole (93mg, 0.582mmol) in N,N-dimethylformamide (1mL) was added and the mixture was stirred for 16 hours, at 5O0C. The solution was cooled to 250C and sodium hydride (60% dispersion in mineral oil, 62mg, 1.55mmol) was added and the solution was stirred for 16 hours at 80C. The reaction mixture was then cooled to 25C and quenched with water (3mL), concentrated in vacuo and the aqueous residue was partitioned between ethyl acetate (2OmL) and water (5mL). The aqueous layer was separated and extracted with ethyl acetate (2x20mL). The combined organic solution was washed with brine (1OmL), concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with pentane: (ethyl acetate:methanol;0.88ammonia, 90:10:1), 3:1 to 1:1. The product containing fractions were evaporated under reduced pressure and the residue was further purified using an Isolute SCX-2 cartridge, eluting with methanol followed by 1M ammonia in methanol. The basic fractions were evaporated to afford the title compound as a yellow gum in 32% yield, 61mg.1HNMR(400MHz, CD3OD) delta: 1.03(s, 3H), 1.08(s, 3H), 1.28-1.31(m, 2H), 1.76-1.80(m, 1H), 1.86-1.93(m, 1H), 2.09-2.18(m, 1H), 2.49-2.63(m, 2H), 2.67-2.70(m, 1 H), 2.76-2.87(m, 2H), 3.80(s, 3H), 4.71-4.75(m, 1H), 6.74-6.77(dd, 1H), 6.89-6.95(dd, 1H), 7.24-7.46(m, 10H), 8.45- 8.59(m, 1 H); LRMS APCI m/z 489 [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 2267-25-6, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2267-25-6, 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. 2267-25-6 name is 2-Chloro-4-fluoroanisole, 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.

PREPARATION EXAMPLE 67 Preparation of 4-chloro-2-fluoro-5-methoxybenzyl chloride (Intermediate No. 15-15) 17.6 g (0.11 mol) of 2-chloro-4-fluoroanisole was dissolved in a dichloromethane solution of 1N titanium tetrachloride, and 88.3 g (1.10 mol) of methoxymethyl chloride was dropwise added thereto at room temperature, followed by stirring at room temperature for 5 hours. after completion of the reaction, the reaction solution was poured into water, followed by stirring at room temperature for 2 hours, and then the aqueous phase was removed. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. Then, the obtained residue was purified by silica gel column chromatography to obtain 15.5 g (yield: 68%) of the desired product. 1 H-NMR (300 MHz,CDCl3) deltavalue: 3.89(3H,s), 5.00(2H,s), 6.97(1H,d), 7.18(1H,d)ppm

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-4-fluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6048823; (2000); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, 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. Safety of 2-Chloro-4-fluoroanisole

2-Chloro-4-fluoro-1-methoxybenzene a8 (0.0160 g, 0.10 mmol), acridine photosensitizer (A) (0.0029 g, 0.005 mmol) and L-valine were added sequentially under argon atmosphere. Ethyl b1 (0.0218 g, 0.15 mmol), 1,2-dichloroethane (DCE) 2.0 mL.The reaction was irradiated for 48 hours under a 6W blue light at room temperature.After completion of the reaction, the solvent was evaporated under reduced pressure and purified by column chromatography, eluting solvent: (V) petroleum ether / (V) ethyl acetate = 20/1.A yellow liquid (25) (0.0191 g, 87%) was obtained.

The synthetic route of 2-Chloro-4-fluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central China Normal University; Zhou Shaolin; Shi Weimin; (27 pag.)CN110294685; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, 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. Recommanded Product: 2-Chloro-4-fluoroanisole

To concentrated sulfuric acid (100mL) solution of2-chloro-4-fluoro anisole (38g, 237mmol), bromine (19mL, 737mmol) was addedunder ice-cooling, and the mixture was stirred for 1.5 hours. the reactionsolution was added gradually into ice water and extracted with diethyl ether(300mL × 3). After washing the organic layer with 5% aqueous sodium thiosulfatesolution (300 mL), the organic layer was dried over anhydrous magnesiumsulfate, filtered, and the crude product obtained through concentration underreduced pressure was purified by silica gel chromatography (hexane: ethylacetate = 1 : 0~10: 1) to give white solid of 5-bromo-2-chloro-4-fluoro anisole(8.0 g, yield: 14%) and white solid of 2-bromo-6-chloro-4- fluoro anisole (16.7g, yield: 30%).

The synthetic route of 2-Chloro-4-fluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (75 pag.)JP2016/56157; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2267-25-6, name is 2-Chloro-4-fluoroanisole, molecular formula is C7H6ClFO, 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. Application In Synthesis of 2-Chloro-4-fluoroanisole

Sodium hydride (60% dispersion in mineral oil, 31 mg, 0.776mmol) was added to an ice- cooled solution of the product of preparation 20 (135mg, 0.388mmol) in N1N- dimethylformamide (4mL) and the mixture was stirred at O0C for 15 minutes. 2-chloro-4-fluoro- anisole (93mg, 0.582mmol) in N,N-dimethylformamide (1mL) was added and the mixture was stirred for 16 hours, at 5O0C. The solution was cooled to 250C and sodium hydride (60% dispersion in mineral oil, 62mg, 1.55mmol) was added and the solution was stirred for 16 hours at 80C. The reaction mixture was then cooled to 25C and quenched with water (3mL), concentrated in vacuo and the aqueous residue was partitioned between ethyl acetate (2OmL) and water (5mL). The aqueous layer was separated and extracted with ethyl acetate (2x20mL). The combined organic solution was washed with brine (1OmL), concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with pentane: (ethyl acetate:methanol;0.88ammonia, 90:10:1), 3:1 to 1:1. The product containing fractions were evaporated under reduced pressure and the residue was further purified using an Isolute SCX-2 cartridge, eluting with methanol followed by 1M ammonia in methanol. The basic fractions were evaporated to afford the title compound as a yellow gum in 32% yield, 61mg.1HNMR(400MHz, CD3OD) delta: 1.03(s, 3H), 1.08(s, 3H), 1.28-1.31(m, 2H), 1.76-1.80(m, 1H), 1.86-1.93(m, 1H), 2.09-2.18(m, 1H), 2.49-2.63(m, 2H), 2.67-2.70(m, 1 H), 2.76-2.87(m, 2H), 3.80(s, 3H), 4.71-4.75(m, 1H), 6.74-6.77(dd, 1H), 6.89-6.95(dd, 1H), 7.24-7.46(m, 10H), 8.45- 8.59(m, 1 H); LRMS APCI m/z 489 [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 2267-25-6, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2007/34325; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2267-25-6, 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. 2267-25-6, name is 2-Chloro-4-fluoroanisole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-chloro-4-fluoroanisole (38g, 237mmol) concentrated sulfuric acid (100mL) solution, bromine (19mL, 737mmol) was added under ice-cooling, and the mixture was stirred for 1.5 hours. It was added to the reaction solution gradually into ice water, and extracted with diethyl ether (300mL ¡Á 3). After washing the organic layer with 5% aqueous sodium thiosulfate solution (300 mL), the organic layer was dried over anhydrous magnesium sulfate, filtered, and the crude product obtained through concentration under reduced pressure by silica gel chromatography – (hexane: ethyl acetate = 1 : 0 to 10: 1) to give 5-bromo-2-chloro-4-fluoroanisole of a white solid (8.0g, yield: 14%) and 2-bromo-6-chloro-4-fluoroanisole of a white solid (16.7g, yield: 30%)It was obtained.

The synthetic route of 2-Chloro-4-fluoroanisole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; TATENO, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (76 pag.)JP2016/60742; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2267-25-6, The chemical industry reduces the impact on the environment during synthesis 2267-25-6, name is 2-Chloro-4-fluoroanisole, I believe this compound will play a more active role in future production and life.

72-Chloro-4-fluoro-1-methoxybenzene was treated with n-butyllithium and hexachloroethane; the resulting 2,3-dichloro-1-fluoro-4-methoxybenzene was demethylated with boron tribromide to provide the requisite phenol.

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, 2-Chloro-4-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O’Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics