Category: 67567-26-4

67567-26-4, name is 4-Bromo-2,6-difluoroaniline, belongs to bromides-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. name: 4-Bromo-2,6-difluoroaniline

Example 1 5-Bromo-1,3-difluoro-2-nitro-benzene: To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 m]L), stirred at 55 C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55 C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5*100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) delta 7.32 (dt, 2H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Charifson, Paul S.; Deininger, David D.; Grillot, Anne-Laure; Liao, Yusheng; Ronkin, Steven M.; Stamos, Dean; Perola, Emanuele; Wang, Tiansheng; LeTiran, Arnaud; Drumm, Joseph; US2005/256136; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H4BrF2N

Compound 121 : 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-3-fluoro-5-methoxybenzoic acid; [0581] 5-Bromo-l,3-difluoro-2-nitrobenzene: To a mixture of acetic acid (30 mL), 30% H2O2 (20 mL) and concentrated sulfuric acid (1 mL) was added l-bromo-2,6- difluoroaniline (5 g, 24 mmol) in acetic acid (10 mL) dropwise at 85 0C. The reaction mixture was heated for 1 h. It was then cooled down, diluted to water and extracted with ethyl acetate. The organic layer was dried and concentrated to a red residue, which was purified by flash column (EtOAc in Hexane 2-5%) to give the product as yellow solid (2.7 g, 47%). 1H NMR (400 MHz, CHLOROFORM-J) delta ppm 7.33 (m, 2 H).

According to the analysis of related databases, 67567-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/42711; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4,Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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 solution of 1-tert-butoxycarbonyl-4-methyl-piperidine-4-carboxylic acid (240 mg, 0.99 mmol, 1.0 eq.) in CH2Cl2 (8.0 mL) was added pyridine (320 mg, 0.32 mL, 3.9 mmol, 4.0 eq.), (COCl)2 (130 mg, 0.088 mL, 0.99 mmol, 1.0 eq.) followed by 2 drops of DMF. After 1 h at room temperature, 4-bromo-2,6-difluoro-aniline (210 mg, 0.99 mmol, 1.0 eq.) was added and the mixture was stirred at room temperature overnight, after which CH2Cl2 was added and washed with water and brine. The organic layers were dried, evaporated and purified over silica gel with ethyl acetate in hexanes (5 to 50% gradient) to give tert-butyl 4-[(4-bromo-2,6-difluoro- phenyl)carbamoyl]-4-methyl-piperidine-1-carboxylate (350 mg, 82%). 1H NMR (CDCl3) d: 7.43 (s, 1H), 7.11 (d, J= 6.6 Hz, 2H), 3.65 – 3.81 (m, 2H), 3.14 – 3.22 (m, 2H), 2.09 (d, J= 13.9 Hz, 2H), 1.46 – 1.52 (m, 2H), 1.45 (s, 9H), 1.32 (s, 3H).

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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. Quality Control of 4-Bromo-2,6-difluoroaniline

Example 16B V,jV-dibenzyl-4-bromo-2,6-difluorobenzenamineA mixture of the product of Example 16A (1.1 g, 5.3 mmol), benzyl bromide (949 mg, 0.66 ml) and potassium bicarbonate (1.46 mg, 10.6 mmol) in NN-dimethylformamide (3 itiL) was stirred at ambient temperature until TLC indicated no starting material remained. Ethyl acetate was added, and the mixture was washed with water and brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 10/1 petroleumether/dichoromethane to give the title compound.

The synthetic route of 4-Bromo-2,6-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97684; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 67567-26-4 as follows. Computed Properties of C6H4BrF2N

10 kg of 4-bromo-2,6-difluoroaniline (48.08 mol) and 67 L of toluene were charged into a reactor under nitrogen atmosphere and stirred at 20 C. until complete dissolution. 1.67 kg of Pd(PPh3)4 (1.44 mol) were charged and stirred for 10 min. 48 L of a 20 wt. % aqueous solution of Na2CO3 were then charged, followed by the addition of a solution of 3-methoxyboronic acid (8.77 kg, 57.7 mol) in methanol (32 L) over 20 minutes. The mixture was heated at 72 C. for 4 hours and then cooled to 20 C.2) Purification of 3,5-difluoro-3′-methoxybiphenyl-4-amine2.1. A solution of 123 L of a 10% aqueous solution of Na2CO3, 1.5 L of a 25 wt. % aqueous solution of ammonia and 2.0 kg of a filtration resin (Dicalite) were charged to the reactor and the mixture stirred for 5 minutes. The mixture was recirculated through a filter until clarification of the liquors (35 min) and charged into a reactor. 60 L of isopropyl acetate were added and the mixture was stirred for 10 minutes and the phases (A1+O1) were allowed to separate. The aqueous phase (A1) was transferred to a different reactor and 60 L of isopropyl acetate were charged. The mixture was stirred and the phases (A2+O2) were allowed to separate. Both organic phases (O1+O2) were charged into a reactor and 108 L of a 10 wt. % aqueous solution of Na2CO3 were added. The mixture was stirred and the phases (A3+O3) were allowed to separate. The organic phase (O3) was stirred with 108 L of a 10 wt. % aqueous solution of Na2CO3 and the phases (A4+O4) were allowed to separate. The organic phase (O4) was stirred with 100 L demineralised water and the phases (A5+O5) were allowed to separate. The organic phase (O5) was filtered over a filtration resin (Dicalite) in a filter and charged in to a reactor.2.2. Distillation: The organic phase (O5) was distilled during 2 hours under reduced pressure (approx. 750 mm Hg) keeping the distilled mixture at temperature below 65 C.3) Preparation of the Aminium Salt (Step b)The distillation residue was dissolved in 100 L of isopropyl acetate, the mixture was cooled to 0-5 C. and 4.2 L of a 35 wt. % aqueous solution of HCl were added drop-wise until the pH was lower than 2. The aminium salt precipitated as a white solid from the dark brown coloured solution. The slurry was stirred for 2 hours at 0-5 C., filtered and the cake washed twice with 50 L of previously cooled isopropyl acetate. The cake was pulled dry under reduced pressure. 3,5-difluoro-3′-methoxybiphenyl-4-aminium chloride was isolated as beige solid. The weight of the wet-cake was 13.83 kg, equivalent to 10.25 kg of dry product (37.73 mol) which corresponds to a yield of 78.5%.

According to the analysis of related databases, 67567-26-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boix Bernardini, Maria Carmen; US2012/245359; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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. Computed Properties of C6H4BrF2N

To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 mL), stirred at 55 C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55 C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5*100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) delta 7.32 (dt, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67567-26-4, its application will become more common.

Reference:
Patent; Charifson, Paul S.; Deininger, David D.; Grillot, Anne-Laure; Liao, Yusheng; Ronkin, Steven M.; Stamos, Dean; Perola, Emanuele; Wang, Tiansheng; LeTiran, Arnaud; Drumm, Joseph; US2004/235886; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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. Application In Synthesis of 4-Bromo-2,6-difluoroaniline

1b) A suspension of 416 g of 4-bromo-2,6-difluoroaniline, 752 g of benzyl bromide and 608 g of potassium carbonate in 2 l of acetonitrile is refluxed for 48 hours. The mixture is subsequently evaporated in a rotary evaporator, the residue is dissolved in toluene and extracted with hydrochloric acid (10%), the toluene phase is evaporated in a rotary evaporator, and the product is stirred into heptane and stirred with silica gel for about 4.5 hours, filtered with suction and evaporated in a rotary evaporator, giving dibenzyl(4-bromo-2,6-difluorophenyl)amine, yield 85.6%.

The synthetic route of 4-Bromo-2,6-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; US6716491; (2004); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

Set the reflux reaction device, put the stirrer into the reaction flask, Adding 4 – propyl borate, 2,6 – difluoro – 4 – bromoaniline, catalyst Pd (Pph3) 2Cl2, sodium carbonate; Sealing the reaction system, replacing the air in the sealing system into nitrogen; Immediately add isopropanol and water, stir and slowly heat reflux to ensure that the system reacts under nitrogen. After 2.5 hours, the degree of reaction was checked with TLC.

The synthetic route of 67567-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen Chao Duowei Optoelectric Zi Co., Ltd.; Shenzhen Mokerui Optoelectric Zi Institute; Zhang Guoxian; Bao Rui; (19 pag.)CN106397288; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H4BrF2N

Preparation example 5: Preparation of (Z)-N’-(4-bromo-2,6-difluorophenyl)-N-isopropyl acetamidine 4-bromo-2,6-difluroaniline (7.87 g, 37.9 mmol)), N-isopropylacetamide (7.65 g, 75.7 mmol) and triethylamine (5.7 g, 56.9 mmol) were dissolved in toluene (150 mL), and phosphorus oxychloride (5.8 g, 37.9 mmol) was added slowly. After the addition, the mixture was heated to reflux for 3 h. Then, the reaction mixture was cooled to room temperature, the solvent was removed by reduced pressure distillation, and dichloromethane (200 mL) was added. The resultant mixture was washed with saturated sodium hydrogen carbonate solution (2×100 mL) twice, dried by anhydrous sodium sulfate, filtrated under suction, and distilled under reduced pressure, to get the solid title compound (7.3 g, yield: 66.2%).

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; Xuanzhu Pharma Co., Ltd.; WU, Frank; CHEN, Bo; (105 pag.)EP3091008; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, A new synthetic method of this compound is introduced below., Computed Properties of C6H4BrF2N

A mixture suspension of 4-bromo-2,6-difluoroaniline (7, 25.85 g) and copper(I) cyanide (16.70 g) in NMP (60 mL) was stirred at reflux temperature for 1.5 h and then cooled down to room temperature. To the mixture was added 1,2-diaminoethane (23 mL) and the mixture was poured into water (150 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with 10 wt % 1,2-diaminoethane solution in water and water, and then dried. The desiccant was removed by filtration and the filtrate was evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 8 (16.54 g, 86%) as a pale yellow solid: 1H NMR (DMSO-d6) delta 6.36 (2H, s), 7.50 (2H, dd, J = 2.7, 6.7 Hz); EI-MS m/z 154 [(M)+].

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:
Article; Negoro, Kenji; Yonetoku, Yasuhiro; Misawa-Mukai, Hana; Hamaguchi, Wataru; Maruyama, Tatsuya; Yoshida, Shigeru; Takeuchi, Makoto; Ohta, Mitsuaki; Bioorganic and Medicinal Chemistry; vol. 20; 17; (2012); p. 5235 – 5246;,
Bromide – Wikipedia,
bromide – Wiktionary