Category: 111721-75-6

Application of 111721-75-6, A common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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.

In a 50 mL microwave tube, to a solution of 20 mL of 1 ,4-dioxane and 3 mL of water degassed with argon for 15 minutes, were successively added, 900 mg (4.73 mmol) of 2-bromo-3-fluoroaniline, 2.64 g (11.84 mmol) of 3-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine, 1798 mg (11.84 mmol) of cesium fluoride, 216 mg (0.237 mmol) of tris(dibenzylideneacetone)pailadium(0) and 194 mg (0.474 mmol) of S-Phos. The reaction mixture was heated under microwave at 150 C for 1 hour. The cooled reaction mixture was diluted with ethyl acetate and filtered over a pad of Celite. The organic phase was washed by brine and dried over magnesium sulfate. The organic phase was concentrated under vacuo and purified by column chromatography on silica gel (40 g cartridge – gradient n-heptane/ethyl acetate) to yield 775 mg (72%) of 2-(3-fluoropyridin-4-yl)aniline. LogP = 2.38. Mass (M+H) = 207.

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; CRISTAU, Pierre; DESBORDES, Philippe; DUFOUR, Jeremy; GOURGUES, Mathieu; LAMPRECHT, Sybille; LOQUE, Dominique; MEISSNER, Ruth; NAUD, Sebastien; THOMAS, Vincent; (90 pag.)WO2020/79173; (2020); A1;,
Bromide – Wikipedia,
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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 111721-75-6 as follows. Formula: C6H5BrFN

General procedure: Method I. Compounds 1a-1e and 3b were synthesized using a modified procedure.1 Substituted aniline (1.0 equiv.) was added to a round-bottom flask. The flask was fitted with a rubber septum and purged with nitrogen gas, and acetic anhydride (1M in CH2Cl2, 1.1 equiv.) was added at room temperature. The reaction was refluxed overnight and monitored by TLC. Upon completion the reaction mixture was quenched with H2O. The resulting mixture was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anh. Na2SO4, filtered, then concentrated in vacuo to give the product.

According to the analysis of related databases, 111721-75-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lasing, Thitiya; Phumee, Atchara; Siriyasatien, Padet; Chitchak, Kantima; Vanalabhpatana, Parichatr; Mak, Kit-Kay; Hee Ng, Chew; Vilaivan, Tirayut; Khotavivattana, Tanatorn; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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 111721-75-6, Computed Properties of C6H5BrFN

To a solution of 2-bromo-3-fluoroaniline (2.0 g, 11 mmol) in CH2Cl2 (50 mL) was added butyryl chloride (1.3 g, 13 mmol) and pyridine (1.7 g, 21 mmol) at 0 C. The mixture was stirred at room temperature for 24 h. Water (20 mL) was added and the mixture was extracted with CH2Cl2 (50 mL*3). The organic layers were dried anhydrous over Na2SO4 and evaporated under vacuum to give N-(2-bromo-3-fluorophenyl)butyramide (2.0 g, 73%), which was directly used in the next step.

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

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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: 4-Amino-7-X-8-bromo-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).To a solution of 2-[(3-X-2-bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (1.0 equiv) in anhydrous toluene (0.1 M, 1 volume) was added aluminum chloride (3.0 equiv). The reaction was heated with vigorous stirring at 70-90 C for 1-3 h, cooled, and quenched with Rochelle’s salt (saturated aqueous potassium sodium tartrate, 0.5 volume). Afterward, the mixture was stirred at room temperature overnight. The aqueous layer was separated, and the organic layer was treated with fresh Rochelle’ salt (0.5 volume) while stirring at room temperature for 1 h. After separating the resulting layers, the organic suspension was washed with water and filtered to give give a tan solid. Additionally, the organic filtrate was concentrated, and triturated with ether to give a tan precipitate. The resulting solids were filtered to give a tan solid in 30-70% yield of crude product. The combined tan solid was dried at 50 C under high-vacuum to give the title compound, which was used without further purification.The intermediate compounds were prepared as follows:2-[(3-X-2-Bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (X = H or F).Solution A: To a mechanically stirred solution of 3-X-2-bromoaniline (1.0 equiv) in acetic acid (2 M, 1 volume) was added water (0.6 volume) at ambient temperature. The mixture was cooled to 0 C, and then concentrated aqueous HCl (0.5 volume) added. A precipitate was formed immediately and the suspension was stirred at 0 C for 20 min. To this suspension was added dropwise a solution of sodium nitrite (1.10 equiv) in water (0.6 volume), maintaining the internal temperature below 5 C. The resulting clear orange solution was stirred at 0 C for another 30 min.Solution B: To a mechanically stirred solution of N-(alkyl)-2-cyanoacetamide (1.25 equiv) in ethanol (4.5 volume) was added a solution of sodium acetate (1.60 equiv) in water (120 volume), and chilled to between 0 C and -5 C.Solution A was poured into solution B, maintaining the internal temperature below 0 C. An orange precipitate was formed gradually. The mixture was stirred below 0 C overnight, and then the orange precipitate was collected by filtration, washed with water (100 mL × 3), and dried at 50 C under high vacuum to remove water. An orange solid was obtained in greater than 95% yield, which was the ‘E’, and used for the next step without further purification.

Statistics shows that 2-Bromo-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 111721-75-6.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 111721-75-6,Some common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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 stirred solution of 2-bromo-3-fluoro aniline (25.0 g, 131.57 mmol) in dichloromethane (500 mL) at 0 C under nitrogen was added acetic anhydride (18.65 mL, 197.36 mmol). The resulting mixture was warmed to room temperature and stirred for 16 hours. After that, the reaction mixture was diluted water and extracted with dichloromethane (2 x 500 mL). The combined organic phase was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to get compound XlVa (crude), which was taken as such for the next step without further purification. Yield: 25 g, 81.91%. LC- MS Calc. for C8H7BrFNO, 232.05; Obs.; 232.0 [M+]; -NMR (300 MHz, DMSO-d6): delta 9.57 (s, 1H), 7.49-7.34 (m, 2H), 7.20-7.14 (m, 1H), 2.09 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-3-fluoroaniline, its application will become more common.

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; RAMACHANDRAN, Vasanthi; VENKATARAMAN, Balasubramanian; (221 pag.)WO2018/225097; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 111721-75-6, name is 2-Bromo-3-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: bromides-buliding-blocks

This Example made use of the general preparative method designated Route C. 3-Methyl4-nitrobenzoyl chloride (0.2 mol) was added slowly to a solution of 2-bromo-3-fluoroaiiiline (0.2 mol) in pyridine (100 ml). The resulting solution was heated under reflux for 60 min, then poured into water (300 ml). The precipitate was filtered from solution, washed with water (100 ml), followed by methanol to afford a white solid. [00126] Lawesson’s reagent (0.07 mol) was added to a solution of the benzanilide obtained (0.1 mol) in HMPA (50 ml). The resulting solution was heated at 100 C. for 15 hr, then poured into water (300 ml). The product was extracted into diethyl ether (3×300 ml) and washed with water (3×200 ml). Evaporation of the solvent followed by recrystallization from methanol gave a bright orange solid. [00127] Sodium hydride (0.22 mol) was slowly added to a solution of the fluoro substituted thiobenzanilide thus obtained (0.2 mol) in N-methyl-2-pyrrolidinone (2 mol) at room temperature with stirring. The mixture was heated at 150 C. for one hour then allowed to cool. Water (50 ml) was then added and the precipitate collected by filtration and dried in vacuo to give the product as a white solid. [00128] The product of the previous step (0.03 mol) and tin(II) chloride dihydrate (0.15 mol) were suspended in ethanol (150 ml) and heated under reflux for 2 hours. The solvent was removed under vacuum and the resulting oil taken up in ethyl acetate (700 ml). The organic layer was washed with 2 M sodium hydroxide. (2×200 ml), water (100 ml) and salt brine (30 ml). Removal of the solvent under vacuum followed by recrystallization from methanol gave the title compound as a pale yellow solid. [00129] mp 175-177 C.; IR 3021, 1621 (CN), 1470, 1215, 750 cm-1.

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Malcolm, F. G. Stevens; US6858633; (2005); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 111721-75-6, A common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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.

To a solution of 2-bromo-3-fluoroanilinne (2.5 g, 13.2 mmol) and pyridine (1.1 mL, 13.2 mmol) in CH2Cl2 (8 mL) was added dropwise a solution of cinnamoyl chloride (2.3 g, 13.7 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature under argon overnight, diluted with CH2Cl2 and evaporated to dryness. Purification by silica gel chromatography using EtOAc (100 mL). The solution was washed with 1 N HCl (50 mL), sat’d NaHCO3 (50 mL), brine (50 mL) and dried (NaSO4). Evaporation in vacuo afforded the title compound (4.3 g) as a white solid. 1H NMR (300 MHz, CDCl3) delta 6.60 (d, J=15.3 Hz, 1H), 6.92 (t, J=8.1 Hz, 1H), 7.26-7,42 (m, 4H), 7.58 (m, 2H), 7.80 (d, J=15.6 Hz, 2H), 8.36 (d, J=8.4 Hz, 1H)

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ruan, Fuqiang; (35 pag.)US2019/308963; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 111721-75-6, 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. 111721-75-6, name is 2-Bromo-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

5-Amino-7-fluoro-1H-quinolin-2-one; To a solution of 2-bromo-3-fluoroaniline (6.5 g, 34.17 mmol) and pyridine (2.7 g, 34.17 mmol) in 20 ml of CH2Cl2, cinnamoyl chloride (5.95 g, 35.88 mol) in 10 ml CH2Cl2 are added dropwise and mixture was refluxed for 30 min. The reaction mixture is diluted with CH2Cl2, the organic layer washed with diluted HCl, saturated Na2CO3 solution, water, and dried (Na2SO4). The solvent is removed in vacuo to give 10.5 g of N-(2-bromo-3-fluorophenyl)-3-phenylacrylamide. To a solution of N-(2-bromo-3-fluorophenyl)-3-phenylacrylamide (10.5 g, 32.8 mmol) in 70 ml of chlor-benzene at 130 C. AlCl3 (21.9 g, 0.164 mol) is added portionwise, the mixture is stirred at this temperature 2 h and poured in ice-water. The precipitate is filtered off and dried. Yield 6.05 g (76%). 6 g (24.8 mmol) of 8-bromo-7-fluoro-1H-quinolin-2-one are refluxed in 30 mL of POCl3 during 2 h, then poured on ice, extracted with benzene, the benzene extract dried (Na2SO4) to yield 6.1 g 8-bromo-2-chloro-7-fluoroquinoline after solvent removal. To a mixture of 10 ml 10%-oleum and 1.4 g (22.2 mmol) of fuming HNO3 8-bromo-2-chloro-7-fluoroquinoline (4.8 g 18.5 mmol) is added portionwise. The mixture is heated at 100 C. for 2 h. Additional HNO3 (0.17 g) is added and stirred for additional 1 h. The reaction mixture is poured in ice-water, extracted with EtOAc, filtered through silica gel, and crystallized from heptane-toluene to yield 2.3 g (50%) 8-bromo-2-chloro-7-fluoro-5-nitroquinoline. 2.3 g (7.54 mmol) of 8-bromo-2-chloro-7-fluoro-5-nitroquinoline are heated at 100 C. for 5 h in a solution containing 16 ml of CH3COOH, 3.2 ml of H2O and 5 ml of conc. HCl. The mixture is poured in water, the formed precipitate is filtered off, stirred in EtOAc and filtered to yield 1.71 g. 8-bromo-7-fluoro-5-nitro-1H-quinolin-2-one. To a suspension 1.7 g (5.92 mmol) of 8-bromo-7-fluoro-5-nitro-1H-quinolin-2-one and 2.3 g (35.5 mmol) of HCOONH4 in 10 ml of ethanol 0.1 g 10% Pd-C are added, and stirred for 2 h at 60 C. A solid disappeared and then formed again. The precipitate is filtered off, dissolved in 3 ml of DMSO and filtered through silica gel. 15 ml of water are added to the eluate, the precipitate is filtered off and dried to yield 0.5 g (47%) 5-Amino-7-fluoro-1H-quinolin-2-one. 1H-NMR (DMSO-d6); delta=6.14 (dd, 1H), 6.20 (dd, 1H), 6.23 (d, 1H), 6.27 (br, 2H), 8.06 (d, 1H), 11.50 (br., 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-3-fluoroaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Berger, Markus; Rehwinkel, Hartmut; Zollner, Thomas; May, Ekkehard; Hassfeld, Jorna; Schacke, Heike; US2009/137564; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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: Different aniline (0.75 mmol) was dissolved in CH3CN (10 mL) in a 25-mL round-bottomed flask and cooled to 0C in an ice bath. To this stirred mixture was added t-BuONO (1.125 mmol) followed by TMSN3 (0.9 mmol) dropwise. The resulting solution was stirred at room temperature for 2 h. Compound 2 (0.5 mmol), CuI(0.1 mmol) and Et3N (0.6 mmol) were then added and the reaction was stirred at room temperature. The progress of the reaction was monitored by TLC. After the completion of reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluting solution to afford the target compounds 3 [25-29]. The data of 3a-3w are shown as follows. We selected one compound, 3d, as a representative compound and signal positions of carbon protons were assigned.

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Xiulei; Xiao, Youxin; Wang, Gaolei; Li, Zhong; Xu, Xiaoyong; Research on Chemical Intermediates; vol. 42; 6; (2016); p. 5495 – 5508;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 111721-75-6, These common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, 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.

To a stirred solution of 2-bromo-3-fluoroaniline (CAS 111721-75-6, 9.50 g, 50.0 mmol, 1.00eq.) in an aqueous hydrochloric acid solution (12.5 mL conc. HCI in 80.0 mL of water, 150mmol, 3.00 eq.) was added dropwise a 2.5 M solution of sodium nitrite (20.0 mL, 50.0 mmol,1 .00 eq.) in water at a temperature of 0C. After complete addition, a 4.5 M solution of sodiumacetate in water (62.4 mL, 281 mmol, 5.62 eq.) was added via dropping funnel, followed bydropwise addition of ethyl-2-oxocyclopentanecarboxylate (CAS 611-10-9, 7.40 mL, 50.0 mmol,1.00 eq.). The resulting yellow suspension was maintained at 0 C for 15 minutes and thenwarmed to room temperature and stirred for 2 hours. The reaction mixture was extracted thricewith dichloromethane (100 mL each) and the combined organic extracts were dried overmagnesium sulfate, filtered and concentrated under reduced pressure to give the crudehydrazone as a red oil (18.1 g). The residue was dissolved in ethanol (50.0 mL, 1.00 M), afterwhich sulfuric acid (6.63 mL, 125 mmol, 2.50 eq.) was added dropwise. The dark orangesolution was heated at 95 C for 6 days and then cooled to room temperature. The dark brownsolution was poured onto ice/water (200 mL) and extracted thrice with dichloromethane (200mL each). The combined organic extracts were washed with saturated aqueous bicarbonatesolution (200 mL), dried over magnesium sulfate, filtered and concentrated under reducedpressure to give a brown solid. The residue was purified by flash column chromatography (0-30% ethyl acetate/hexane gradient) and then recrystallized from hot ethyl acetate/hexane (9:1)to give the title compound as a light yellow solid (8.35 g, 42%). Rf = 0.22 (15% ethyl acetate/hexane, UV).

Statistics shows that 2-Bromo-3-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 111721-75-6.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; THE BROAD INSTITUTE, INC.; THEDE, Kai; MENGEL, Anne; CHRIST, Clara; KUHNKE, Joachim; JOHANNES, Sarah, Anna, Liesa; BUCHGRABER, Philipp; KLAR, Ulrich; SACK, Ulrike; KAULFUSS, Stefan; FERNANDEZ-MONTALVAN, Amaury, Ernesto; WERBECK, Nicolas; MOeNNING, Ursula; NOWAK-REPPEL, Katrin; WITTROCK, Sven; MCKINNEY, David; SERRANO-WU, Michael, H.; LEMKE, Chris; FITZGERALD, Mark; NASVESCHUK, Christopher; LAZARSKI, Kiel; FERRARA, Steven, James; FURST, Laura; WEI, Guo; MCCARREN, Patrick, Ryan; HARVEY, Rebecca, Ann; (652 pag.)WO2019/96922; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary