Category: ethers-buliding-blocks

366-99-4, name is 3-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 366-99-4

To a stirred suspension of 3-fluoro-p-anisidine (3.00 g, 21 mmol) in CH2Cl2 (10 mL) is added acetic anhydride (2.0 mL, 21 mmol) over 1 h while maintaining the temperature between 25-30¡ã C. using a cold water bath. The solution is then stirred for 2 h at 25¡ã C. Additional 1 mL of acetic anhydride is added to the solution, which is then stirred for an additional 2 h. Hexane (30 mL) is slowly added to the mixture over 1 h. The product is collected by filtration, concentrated in vacuo and dried in oven to give 3.40 g (90percent yield) of N-(3-fluoro-4-methoxyphenyl)acetamide as tan crystals. 1H NMR (400 MHz, CDCl3) delta 7.41, 7.19, 7.11, 6.90, 3.87, 2.16. In a 100 mL, three-necked flask equipped with a thermometer and a dropping funnel chilled in an ice-salt bath, N-(3-fluoro-4-methoxyphenyl)acetamide (3.0 g, 16 mmol) is dissolved in 98percent sulfuric acid, care being taken that the temperature does not rise above 5¡ã C. To this solution 2.6 mL of nitric acid is added dropwise at such a rate that the temperature does not rise above 5¡ã C. After all the nitric acid is added, the viscous orange mass is poured onto 50 g of cracked ice and the mixture is thoroughly stirred. The yellow crystals that separate are filtered off and thoroughly washed with water to yield 3.33 g (89percent yield) of N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide as yellow crystals. 1H NMR (400 MHz, DMSO-d6) delta 10.60, 10.17, 7.75, 7.73, 7.62, 7.59, 4.03, 3.92, 2.06. A suspension of N-(5-fluoro-4-methoxy-2-nitrophenyl)acetamide (3.0 g, 13 mmol) in 38 mL of water, 38 mL of HCl and 15 mL of ethanol is refluxed for 30 minutes. On cooling, crystals that separate are recrystallized from ethanol to yield 0.71 g (29percent yield) of 5-fluoro-4-methoxy-2-nitroaniline as red crystals. 1H NMR (400 MHz, CDCl3) delta 7.68, 6.56, 6.04, 3.87. Example 603 is obtained according to Method F, making non-critical modifications. Yield 60percent. HRMS (ESI) calcd for C12H11FN4O5+H 311.0792 found 311.0798.

Statistics shows that 366-99-4 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-4-methoxyaniline.

Reference:
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
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2752-17-2, These common heterocyclic compound, 2752-17-2, name is 2,2′-Oxydiethanamine, 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.

General procedure: Diester1 (1mmol) and the appropriate diamine2-6 (1mmol) were dissolved in dry methanol (50mL) and sodium methoxide (2mmol) was added. A mixture was stirring for 72hat room temperature. After completion of the reaction (controlled by TLC), the solvent was evaporated under reduced pressure and the oily residue was purified by column chromatography (1-5% MeOH in CH2Cl2). All the macrocyclic products obtained in this way are colourless solids, stable to air. 4.2.1 Macrocycle (R)-714b (0010) Yield: 60% (282mg); [alpha]D25 +86.4 (c=0.1, CH2Cl2); Mp. 245-246C; 1H NMR (400MHz, CDCl3):delta=8.02 (d, J=9.0Hz, 2H), 7.90 (d, J=8.2Hz, 2H), 7.45-7.21 (m, 6H), 7.07 (d, J=8.5Hz, 2H), 6.41 (br s, 2H), 4.60 (d, J=15.6Hz, 2H), 4.36 (d, J=15.6Hz, 2H), 3.71-3.56 (m, 2H), 3.51-3.39 (m, 2H), 3.38-3.27 (m, 2H), 2.97-2.86 (m, 2H); 13C NMR (100MHz, CDCl3):delta=168.5, 152.7, 133.6, 130.2, 129.8, 128.1, 127.2, 125.0, 124.6, 119.6, 114.1, 68.9, 68.7, 38.5; IR (film) 3423, 3294, 3056, 2914, 2866, 1674, 1533, 1507, 1273, 1213, 1094, 808, 735cm-1.

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 2752-17-2.

Reference:
Article; Pikus, Grzegorz; Jurczak, Janusz; Tetrahedron; vol. 72; 16; (2016); p. 1928 – 1932;,
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19056-40-7, name is 4-Bromo-3-methoxyaniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 19056-40-7

Step 1. 5-({[4-bromo-3-(methyloxy)phenyl]amino}methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione: 2,2-dimethyl-1,3-dioxane-4,6-dione (8.5 g, 58 mmol) in trimethyl orthoformate (50 mL, 450 mmol) was refluxed at 105 C for 1 hr. 4-Bromo-3-methoxyaniline (10.5 g, 50.4 mmol) was then added and refluxing was continued for and additional hour. The suspension was filtered, and the solid was washed with MeOH and vacuum dried to yield 5-({[4-bromo-3-(methyloxy)phenyl]amino}methylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (17 g, 49 mmol, 96 % yield). 1H NMR (400 MHz, DMSO-d) delta ppm 1.68 (s, 6H), 3.90 (s, 3H), 7.11 (dd, J = 8.6 Hz, 2 Hz, 1H), 7.43 (d, J= 2 Hz, 1H), 7.59 (d, J= 8.6 Hz, 1H), 8.64 (s, 1H), 11.23 (br. s., 1H).

Statistics shows that 19056-40-7 is playing an increasingly important role. we look forward to future research findings about 4-Bromo-3-methoxyaniline.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; HAILE, Pamela, A.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SINGHAUS, Robert, R.; WANG, Gren, Z.; (83 pag.)EP2680844; (2016); B1;,
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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. 101-55-3 name is 1-Bromo-4-phenoxybenzene, 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. 101-55-3

A mixture of compound (III) (Pgi = Pg2 = Boc) (837 mg, 2.00 mmol), PdCl2 (35 mg, 0.20 mmol), 4,4?-di(tert-butyl)-2,2?-bipyridine (54 mg, 0.20 minol), Cs2CO3 (716 mg, 2.20 rnmol), 1-bromo-4-phenoxybenzene (548 mg, 2.20 mmol) and diglyme (10 ml) was heated in a sealed tube under argon atmosphere at 110C for 20 h with intensive stirring. After completion of the reaction the tube was cooled to room temperature, carefully opened, and the reaction mass was poured into EtOAc (40 ml). After intensive stirring for 5 mm the obtained suspension was filtered through celite un evaporated in vacuum. The product was purified by column chromatography (eluent EtOAc-hexane 1:4, Rf 0.3). Yield 727 mg (62%), white amorphous powder.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-phenoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; LEBEDEVS, Antons; PONOMARJOVS, Jurijs; VARACEVA, Larisa; CERNAKS, Dmitrijs; CERNOBROVIJS, Aleksandrs; LAVRINOVICS, Edvards; (15 pag.)WO2017/39425; (2017); A1;,
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Some common heterocyclic compound, 4698-11-7, name is 10-Methoxy-5H-dibenzo[b,f]azepine, molecular formula is C15H13NO, 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. 4698-11-7

Example 2 Step 1. Preparation of 10-Methoxy-5H-dibenz [b, f] azepine-5-carbonyl chloride 100 gms of 10-Methoxy iminostilbine is dissolved in 300 mi chloroform & cooled to 0C. 65 gms of Bis (trichloro methyl) carbonate (BTC) is added to the solution followed by the addition of 54 gms of Dimethyl aniline in 100 mi chloroform over a period of 4 hours maintaining the temperature-0-5C.-T–he-temperature is then maintained 0-10C & maintained for 2 hours. The reaction mixture is poured into 300 mi water & layers are separated. Chloroform is evaporated & product is isolated in methanol. Yield obtained is 104 gms (82% of theoretical).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4698-11-7, its application will become more common.

Reference:
Patent; AMOLI ORGANICS LTD.; WO2005/66133; (2005); A2;,
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Adding some certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-methoxyaniline, 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 19056-40-7. 19056-40-7

Method 12 2-[(4-Bromo-3-methoxyphenyl)diazenyl]-2-cyanoacetamide. Sodium nitrite (8.54 g, 123.7 mmol) dissolved in water (100 ml) was added to an ice- cold suspension of 4-bromo-3-methoxyaniline (25 g, 123.7 mmol) in concentrated HCl (46 ml, 1514 mmol) and water (100 ml). After stirring for 10 minutes, 2-cyanoacetamide (10.40 g, 123.7 mmol) and sodium acetate trihydrate (84 g, 617 mmol) in water (1.8 L) was added and the reaction was allowed to stir overnight. The resulting solid was collected by filtration, washed with water, dried, giving an orange solid which was refluxed in 1.4 L of ethanol for 30 min. The mixture was cooled to room temperature, the solid was collected by filtration, washed with ethanol (100 ml x 3), and dried to yield the title compound as a yellow solid (34.4 g, 94 percent). 1H NMR: 11.70 (s, 1 H), 7.90 (s, 1 H), 7.50 (m, 2 H), 7.35 (s, 1 H), 7.20 (d, 1 H), 3.90 (s, 3 H); m/z: 296.

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 4-Bromo-3-methoxyaniline.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/90353; (2008); A1;,
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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. 32338-02-6, name is 2-Bromo-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 32338-02-6

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 ¡ãC for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

The synthetic route of 32338-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Adding a certain compound to certain chemical reactions, such as: 19056-40-7, name is 4-Bromo-3-methoxyaniline, belongs to ethers-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 19056-40-7, 19056-40-7

2,2-Dimethyl-1,3-dioxane-4,6-dione (8.5 g, 58 mmol) in trimethyl orthoformate (50 mL, 450mmol) was refluxed at 105C for 1 hr. 4-Bromo-3-methoxyaniline (commercially available from, for example, Aldrich) (10.5 g, 50.4 mmol) was then added and refluxing was continued for an additional hour. The suspension was filtered, and the solid was washed with methanol and vacuum dried to yield the title compound (17.0 g, 49 mmol, 96 % yield). LCMSRT= 1.10mm, ES-i-ye 356,358

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-Bromo-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HARLING, John David; SMITH, Ian Edward David; (79 pag.)WO2016/169989; (2016); A1;,
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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. 321-28-8, name is 1-Fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 321-28-8

Step 1: Preparation of 3′-fluoro-4′-methoxy-acetophenone. Acetyl chloride (51.0 g, 0.65 mol) was added dropwise to a stirred solution of aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL), maintaining the temperature between 5-10 C. The mixture was stirred for 10 minutes at 5 C. before the dropwise addition of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92-94 C.

The synthetic route of 321-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US5990148; (1999); A;,
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