Category: 67567-26-4

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. name: 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

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. Computed Properties of C6H4BrF2N

4-bromo-2,6-difluoroaniline (31.05 g, 0.15 mol)N-isopropylacetamide (30.3 g, 0.30 mmol),Phosphorus oxychloride (20.9 mL, 0.225 mol) was added successively to anhydrous toluene.Triethylamine (31.3 mL, 0.225 mol) was slowly added dropwise to the reaction flask in a constant pressure funnel under ice-Keep the internal temperature less than 60 C.The reaction flask was transferred to an oil bath and heated to solvent reflux.After 2 hours the reaction flask was cooled to room temperature,Slowly poured into a 300 g ice-water mixture,Add 300 ml of ethyl acetate,After mixing well,The aqueous layer was again extracted with 200 ml of ethyl acetate,Combined organic layer,After washing with saturated brine, dried over anhydrous sodium sulfate,Concentrated under reduced pressure to obtain a pale yellow solid,Add 100 ml of petroleum ether beating for 10 minutes,The compound of formula IX-1 (28.0 g) was filtered off under reduced pressure,As an off-white solid (yield 92.3%).

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

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Zhang, Yinsheng; Liu, Yingshuai; Li, Li; Miao, Lei; Xu, Tongjie; Liu, Haiyan; Ma, Xueqin; Yu, Sen; Xu, Hongjiang; (49 pag.)CN106467517; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature 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.

Example 1; 2-(6-TERT-BUTYLPYRlDIN-3-YL)-N-((1 R)-1-(3.5-DIFLUORO-4-r(METHYLSULFONYL’)AMINOlPHENYL> ETHYL^-METHYLCYCLOPROPANECARBOXAMIDE; 1A^ N-(4-BROMO-2,6-DIFLUOROPHENYLMETHANESULFONAMIDE; To a solution of 4-bromo-2,6-difluoroaniline (3.0 g, 14.4 mmol) in pyridine (20 ml) was added methanesulfonyl chloride (2.23 ml, 28.8 mmol) at room temperature. Then the mixture was stirred at 50 0C for 6 hours. After cooing to room temperature, the mixture was concentrated in vacuo. The resulting residue was dissolved in THF (40 ml). To this solution was added 2M sodium hydroxide aqueous solution (40 ml) and the reaction was stirred at room temperature for 4 hours. The mixture was acidified with 2M HCI aqueous solution and extracted with EtOAc. The organic layer was washed with2M HCI aqueous solution and brine, dried over sodium sulfate and concentrated in vacuo, to give the title compound (4.05 g, 98%) as an orange solid.1H NMR (270 MHz, CDCI3) delta 3.22 (3H, s), 6.08 (1 H, br s), 7.17-7.24 (2H, m).MS (ESI) m/z 286 (M + H)+,284 (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 4-Bromo-2,6-difluoroaniline, its application will become more common.

Reference:
Patent; PFIZER JAPAN INC.; PFIZER INC.; WO2007/129188; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 67567-26-4, 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.

To 4-bromo-2,6-difluoroaniline (1.0 g, 4.81 mmol) and copper (I) cyanide (1.28 g, 14.3 mmol) was added DMF (10 mL) under nitrogen and the resulting mixture was heated at 160 C for 18 h. After 18 h, the mixture was cooled, poured onto a 12% aqueous ammonia solution and extracted with EtOAc (2X). The combined organic extract was washed with water. The organic phase was combined with a little water and was filtered through celite to remove suspended solids. The organic phase was then separated from the water, then washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography (12% EtOAc/ hexanes eluent) provided 4-amino-3,5-difluorobenzonitrile as a white solid. 1H NMR (300 MHz, Chloroform-d) delta 7.19 – 7.14 (m, 2H), 4.29 (br. s, 2H).

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; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4, 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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The starting materials 1 and 2 were commercially available (Energy Chemical, Shanghai, China).Compound 2 (3.72 mmol) was added to a stirred solution of compound 1 (3.38 mmol) in glacial aceticacid (10 mL). The reaction mixture was then stirred at 110 C for 4 h. After completion of the reaction,the solvent was evaporated, and the residue was purified on a silica gel column chromatography andeluted with ethyl acetate/petroleum ether (bp 60-90 C) (1:3, v/v) to give compounds 3.

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-2,6-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gao, Wei; Li, Xiaotian; Ren, Da; Sun, Susu; Huo, Jingqian; Wang, Yanen; Chen, Lai; Zhang, Jinlin; Molecules; vol. 24; 23; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 67567-26-4, 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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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.

A mixture of 4-bromo-2,6-difluoro-aniline (4.16 g, 20.0 mmol, 1.00 eq.) and ethoxycarbothioylsulfanyl potassium (7.69 g, 48.0 mmol, 2.40 eq.) in DMF (25 mL) was stirred at 130C overnight, then cooled to room temperature, diluted with 1 N HCl (150 mL) and stirred at room temperature for 1 h. The resulting solid was filtered and washed with water and dried. The resulting material was suspended in CH2Cl2 (25 mL) and SO2Cl2 (27.5 g, 16.5 mL, 200 mmol, 10.0 eq.) was added slowly and stirred at room temperature for 48 h. Water was added slowly at 0 C to quenched the reaction. The resulting precipitate was collected by filtration and purified over silica with ethyl acetate in hexanes (2 to 10% gradient) to give 6-bromo-2-chloro-4-fluoro- 1,3-benzothiazole (5.08 g, 95.3%). MS m/z 266.1, 268.0, 270.0 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

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

Adding a certain compound to certain chemical reactions, such as: 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, belongs to bromides-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 67567-26-4, Safety of 4-Bromo-2,6-difluoroaniline

a) 2,6-DifIuoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline A solution of 4-bromo-2,6-difluoroaniline (2.50 g, 12.02 mmol, 1.0 eq), bis(pinacolato)diboron (3.36 g, 13.22 mmol, 1.1 eq), Pd(dppf)CI2 (150 mg, 0.18 mmol, 15 mol %) and potassium acetate (3.54 g, 36.06 mmol, 3.0 eq) in DMSO was heated at 80C under nitrogen for 90 minutes. The reaction mixture was partitioned between EtOAc (100 mL) and saturated aqueous bicarbonate (100 ml_). The organic layer was washed with brine (3 x 100 mL), dried over MgS04 and concentrated in vacuo to give a brown solid (3.0 g, 97%); H NMR (400 MHz, DMSO-d6) delta ppm 6.94-7.07 (m, 2H), 5.66 (s, 2H), 1.17-1.28 (m, 12H); m/z (ES+APCI)+: 256 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4, 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. 67567-26-4, name is 4-Bromo-2,6-difluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Potassium acetate (3.54g, 36.1 mmol) and the boronate (3.36g, 13.2 mmol) were added as solids to a flask then placed under N2. 4-bromo-2,6-difluoroaniline (2.5Og, 12.0mmol) in DMSO (3OmL) was then added to the flask. The reaction was taken through three purge-fill cycles using high vacuum then nitrogen. Pd(dppf)CH2Cl2 (0.129g, 0.159mmol) was added.The reaction was again placed under vacuum then blanketed with nitrogen. The reaction was heated at 80 0C until TLC showed the complete consumption of starting bromide (approximately 90 minutes). The reaction was cooled to room temperature. ETOAc was added, the reaction was then partitioned between EtOAc and saturated aqueous bicarbonate. The organic layer was washed with brine seven times to remove DMSO. The material was then dried with Na2SO4 and concentrated under vacuum. . The residue was chromatographed with eluent 0-100% v/v CEbCVHexanes. Pure product was obtained in 62% yield. 1H-NMR (OMSO-d6) delta 7.03 (dd, J = 6.6Hz, 1.8Hz, 2H), 5.76 (s, 2H) 1.26 (s, 12H); MS [M+H]+ = 256.3, LCMS RT = 3.30 min; R/= 0.37 in 40% CH2Cl2/ Hexanes.

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-2,6-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64931; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 67567-26-4, 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.

A mixture of 4-bromo-2,6-difluoroaniline (2.62 g, 12.6 mmol), methanesulfonyl chloride (1.73 g, 15.1 mmol) and 4-(dimethylamino)pyridine (461 mg, 3.78 mmol) in anhydrous pyridine (35 ml) was stirred for 15 hours at ambient temperature. The mixture was diluted with ethyl acetate (15 ml) and washed with 2M hydochloride aqueous solution until the aqueous pH 2, brine, dried over sodium sulfate. After filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give a residue, which was applied to a silica gel chromatography column and eluted with hexane/ethyl acetate =5/1 to furnish 2.20 g (48 % yield) of the title compound as a white solid. 1H NMR (DMSO-d6, 270 MHz) delta ppm 3.55 (6H, s), 7.78-7.85 (2H, m)

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

Reference:
Patent; Pfizer, Inc.; US2006/100460; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature 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.

The starting material was prepared as follows: Sodium hydride (60%, 612mg, 15.3mmol) was added to a solution of 4-bromo-2,6-difluoroaniline (2.77g, 6.65mmol) in DMF (80ml). After stirring for 30 minutes at ambient temperature, 7-benzyloxy-4-chloro-6-methoxyquinazoline (2g, 6.65mmol), (prepared, for example, as described in WO 97/22596, Example 1, but the free base was generated prior to use), was added and stirring was maintained for 4 hours. The mixture was partitioned between ethyl acetate and water (200ml). The organic layer was separated, washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was triturated with isopropanol, collected by filtration, washed with ether and dried under vacuum to give 7-benzyloxy-4-(4-bromo-2,6-difluoroanilino)-6-methoxyquinazoline (1.95g, 62%). MS – ESI: 472-474 [MH]+ 1H NMR Spectrum: (DMSOd6) 3.94 (s, 3H), 5.3 (s, 2H), 7.3 (s, 1H), 7.4 (d, 1H), 7.45 (t, 2H), 7.5 (s, 1H), 7.55 (d, 1H), 7.65 (d, 2H), 7.85 (s, 1H), 8.35 (s, 1H), 9.4-9.6 (br s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2,6-difluoroaniline, its application will become more common.

Reference:
Patent; AstraZeneca AB; EP1244647; (2006); B1;,
Bromide – Wikipedia,
bromide – Wiktionary