Category: 4863-91-6

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-fluoroaniline, belongs to chlorides-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 4863-91-6, COA of Formula: C6H5ClFN

Example 1: Synthesis of N-(3-chloro-5-fluorophenyl)-4 nitrobenzo[c] [1,2,5] oxadiazol-5-amine Compound 1 [093] 5-Chloro-4-nitrobenzo[c][l,2,5]oxadiazole (1 15 mg, 0.58 mmol) was combined with 3-chloro-5-fluoroaniline (83.7 mg, 0.58 mmol) in DMF (0.55 mL), and the mixture was heated at 110C for 1.25 hours. The mixture was cooled to ambient temperature, resulting in the formation of a solid mass. This solid was resuspended in ethyl acetate and transferred to a larger volume of ethyl acetate (100 mL). This was sonicated to completely dissolve the solids. The organic layer was washed 5 times with water (50 mL) and brine, separated, and dried over Na2S04, then filtered and concentrated in vacuo. The resultant yellow solid was resuspended in ethyl acetate (3 mL), and filtered. The solids were washed with fresh ethyl acetate, and air-dried. N-(3-chloro-5-fluorophenyl)-4-nitrobenzo[c][l,2,5]oxadiazol-5-amine was obtained as a free-flowing yellow solid, (122 mg, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 4863-91-6, 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. 4863-91-6 name is 3-Chloro-5-fluoroaniline, 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) 4-Bromo-3-chloro-5-fluoroaniline3- Chloro-5-fluoroaniline (2061 mmol, 300 g) was dissolved in ACN (3000 ml) and the solution cooled to 0C. NBS (2061 mmol, 367 g) was added to the reaction mixture in small portions keeping the temperature below 10 C. Reaction mixture was stirred at 10 +/- 5 C for 3.5 h. 10 % Aqueous NaHS03 was added and the reaction mixture was concentrated under vacuum to remove organic solvents. Water and DCM was added, stirred for 15 min and the phases were separated. The water phase was extracted with DCM. The combined organics were washed with water. The organic phase was evaporated. 2-Propanol was added to the residue and distilled until the steam temperature was 80 C. Water was added and the temperature was kept at 40 +/- 10 C. The mixture was cooled to 5 C and stirred for 4 h. The precipitate was removed by filtration, washed with water and dried under vacuum. 440.7 g of the title compound was obtained. 1 H-NMR (400 MHz, DMSO-c/6): delta 5.87 (s, 2H), 6.42-6.49 (m, 1H), 6.62-6.66 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; ORION CORPORATION; TOeRMAeKANGAS, Olli; WOHLFAHRT, Gerd; SALO, Harri; RAMASUBRAMANIAN, Rathna, Durga; PATRA, Pranab, Kumar; MARTIN, Arputharaj, Ebenezer; HEIKKINEN, Terhi; VESALAINEN, Anniina; MOILANEN, Anu; KARJALAINEN, Arja; WO2012/143599; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-fluoroaniline, belongs to chlorides-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 4863-91-6, Application In Synthesis of 3-Chloro-5-fluoroaniline

EXAMPLE A-12 N-(3-chloro-5-fluorophenyl)-N’-t-pentylthiourea A solution of 8.5 g of 3-chloro-5-fluoroaniline in 150 ml of benzene was refluxed. To the solution was added 2.2 g of thiophosgene in 10 ml of benzene dropwise with stirring. The mixture was stirred at the same temperature for 3 hours, cooled to room temperature and filtered to remove insoluble matter. The filtrate was evaporated in vacuo and filtered again to remove insoluble matter. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography using n-hexane as a solvent. The resulting oil was dissolved in 30 ml of benzene and reacted with 3.4 g of t-pentylamine with stirring at room temperature for 30 minutes. The reaction mixture was evaporated in vacuo and the resulting solid recrystallized from cyclohexane to give 2.2 g of the title compound as colorless needles melting at 116.0-117.5 C. NMR (DMSO-d6, delta ppm): 0.82 (3H, t), 1.42 (6H, s), 1.93 (2H, q), 7.0-7.1 (1H, m), 7.4-7.7 (3H, m), 9.58 (1H, bs).

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, 3-Chloro-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kanebo, Ltd.; US5087640; (1992); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4863-91-6, 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. 4863-91-6, name is 3-Chloro-5-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j00196j To 4-chlorophenacyl chloride (1.0 g, 5.3 mmol) in anhydrous acetonitrile (15 mL) under a nitrogen atmosphere was added potassium thiocyanate (0.57 g, 5.8 mmol). The suspension was stirred at ambient temperature for 2.5 hours. Next, to the suspension was added 3-chloro-5-fluoroaniline (0.85 g, 5.8 mmol), and the resulting mixture was stirred at ambient temperature for 2 hours. Then, water (30 mL) was slowly added to the reaction mixture, and the resulting mixture was slurried for 20 minutes. The solids were collected by filtration and washed with water then dried in vacuo to yield the title compound (1.72 g, 9 1%).

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, 3-Chloro-5-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYCERA CORPORATION; HURD, Alexander, R.; TAYLOR, Clarke, B.; TOOGOOD, Peter, L.; VAN HUIS, Chad, A.; WO2013/185046; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4863-91-6,Some common heterocyclic compound, 4863-91-6, name is 3-Chloro-5-fluoroaniline, molecular formula is C6H5ClFN, 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) 4-Bromo-3-chloro-5-fluoroaniline 3-Chloro-5-fluoroaniline (2061 mmol, 300 g) was dissolved in ACN (3000 ml) and the solution cooled to 0 C. NBS (2061 mmol, 367 g) was added to the reaction mixture in small portions keeping the temperature below 10 C. Reaction mixture was stirred at 10+-5 C. for 3.5 h. 10% Aqueous NaHSO3 was added and the reaction mixture was concentrated under vacuum to remove organic solvents. Water and DCM was added, stirred for 15 min and the phases were separated. The water phase was extracted with DCM. The combined organics were washed with water. The organic phase was evaporated. 2-Propanol was added to the residue and distilled until the steam temperature was 80 C. Water was added and the temperature was kept at 40+-10 C. The mixture was cooled to 5 C. and stirred for 4 h. The precipitate was removed by filtration, washed with water and dried under vacuum. 440.7 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): delta 5.87 (s, 2H), 6.42-6.49 (m, 1H), 6.62-6.66 (m, 1H).

The synthetic route of 4863-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORION CORPORATION; Toermakaengas, Olli; Wohlfahrt, Gerd; Salo, Harri; Ramasurbamanian, Rathna Durga; Patra, Pranab Kumar; Martin, Arputharaj Ebenezer; Heikkinen, Terhi; Vesalainen, Anniina; Moilanen, Anu; Karjalainen, Arja; US2014/94474; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 4863-91-6, name is 3-Chloro-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

A mixture of Example A47 (200 mg, 0.363 mmol), DIEA (188 mg, 1.452 mmol) and 3-chloro-5-fluoroaniline (211 mg, 1.452 mmol) in dioxane (5 mL) was heated at 80 C. overnight. The mixture was cooled to RT, treated with EtOAc and satd. NaHCO3 and the resulting solid collected via filtration and dried to afford crude 1-(4-chloro-5-(1-ethyl-7-((4-methoxybenzyl)(methyl)amino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-(3-chloro-5-fluorophenyl)urea (91 mg, 39% yield) which was carried on to the next step without further purification. MS (ESI) m/z: 638.2 [M+H]+.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Petillo, Peter A.; US8461179; (2013); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 4863-91-6, 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 4863-91-6 as follows.

Example 9: Synthesis of Compound 38 Compound 38 [0111] A flame-dried flask was charged with 5-chlorobenzo[c][l,2,5]oxadiazole (100.0 mg, 0.65 mmol, 1 equiv) and toluene (3mL), and the mixture was stirred at 1 10 C for 30 min with a reflux condenser. The solution was cooled to room temperature, and the flask was charged sequentially with palladium (II) acetate (8.8 mg, 0.040 mmol, 6 mol%), racemic 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (24.9 mg, 0.040 mmol, 6 mol%), 2-chloro-4- fluoroaniline (68.4 mu,, 0.65 mmol, 1 equiv) and potassium tert-butoxide (80.0 mg, .71 mmol, 1.1 equiv). The mixture was stirred at 90 C for 12 h, cooled to room temperature, and diluted with water. The mixture was washed with dichloromethane (3x). The combined organic layers were washed with IN HC1, IN NaOH, and brine. The organic layers were then dried over MgS04 and concentrated under reduced pressure. The resulting solid was then recrystallized in hexanes to provide compound 38 as a brown solid (67 mg, 39% yield): XH NMR (400 MHz, Acetone-d6) 8.59 (bs, 1H), 7.87 (d, J = 9.2 Hz, 1H), 7.40 (dd, J= 2.0 Hz, 9.6 Hz, 1H), 7.31 (m, 1H), 7.20 (s, 1H), 7.12 (dt, J= 1.3 Hz, 12.0 Hz, 1 Hz), 6.92 (dt, J= 2.0 Hz, 8.6 Hz, 1H); 13C NMR (100 MHz, Acetone-d6) 164.4 (d, J = 245.3 Hz), 151.1, 147.9, 145.4, 144.9 (d, J = 1 1.9 Hz), 136.3 (d, J = 13.2 Hz), 131.0, 118.2, 1 16.3, 1 10.6 (d, J = 25.5 Hz) 105.9 (d, J= 25.0 Hz), 91.7; LCMS (ESI) calc’d for [Ci2H6ClFN30]”([M-H]”): m/z 262.0, found 262.0.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-fluoroaniline, belongs to chlorides-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 4863-91-6, Application In Synthesis of 3-Chloro-5-fluoroaniline

To a solution of compound 37.3 (1 eq) in toluene (37 eq) cooled in an ice water bath was added N,N,N’,N’-te¡êramethylethylenediamine (3 eq) and chlorotrimethylsilane (4 eq) the reaction mixture was allowed to come to rt for 30 min. Iodine (1.2 eq) was added portion wise at 10 C. After the addition of iodine was complete the reaction mixture stirred at RT for 3 h followed by diluting with EtOAc and washing with aq a2S204, dried over Na2SC>4 and concentrated in vacuo to afford a residue. To a solution of 3-chloro-5-fluoroaniline (2 eq) in THF (40 eq) was added sodium hydride (60% oil dispersion in mineral oil 3 eq) and stirred at RT for 15 min. Added a solution of the above residue in THF (10 mL) and stirred at RT for 2 h followed by diluting with EtOAc and washing with 5% citric acid, dried over Na2SC>4 and the solvent removed in vacuo. The residue was purified by flash chromatography (10% EtOAc/Hexane to 100% EtOAc) to povide compound 37.4 (48% yield) as a white foam. EIMS (m/z): calcd. for C21H28CIF2N3O3 (M++Na) 466.92, found 466.00.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4863-91-6, 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. 4863-91-6 name is 3-Chloro-5-fluoroaniline, 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.

Example 4: Synthesis of Compound 33 33 Compound 33 Compound 33 [099] A flame-dried flask was charged with 2-bromonitrobenzene (50 mg, 0.25 mmol, 1 equiv) tris(dibenzylideneacetone)dipalladium (11.3 mg, 0.0012 mmol, 5 mol%), racemic 2,2′- bis(diphenylphosphino)-l, l’-binaphthyl (11.5 mg, 0.0019 mmol, 7.5 mol%), and cesium carbonate (163.1 mg, 0.50 mmol, 2 equiv). The flask was degassed and purged with nitrogen. Toluene (2.88 mL) was added, followed by 2-chloro-4-fluoroaniline (35.3 mg, 0.25 mmol, 1 equiv). The reaction was heated to 100C with a reflux condenser and stirred for 12 h. The mixture was cooled to room temperature, filtered through a pad of celite, dried over MgS04 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (9: 1 hexanes:ethyl acetate) afforded the desired aniline 33 as an orange solid (58 mg, 88% yield): XH NMR (400 MHz, Acetone-d6) 9.27 (bs, 1H), 8.18 (d, J= 8.5 Hz, 1H), 7.63 (d, J = 8.6 Hz, 1H), 7.52 (d, J = 8.6 Hz, 1H), 7.28 (s, 1H), 7.17 (dt, J= 2.2 Hz, 10.4 Hz, 1H), 7.04 (m, 2H); 13C NMR (100 MHz, Acetone-d6) 164.2 (d, J = 245.7 Hz), 144.0 (d, j = 1 1.8 Hz), 140.9, 136.7, 136.6, 136.2 (d, J= 13.0 Hz), 127.2, 120.7, 1 18.9, 1 18.9, 1 12.0 (d, J= 25.4 Hz), 108.6 (d, J = 24.5 Hz);LCMS (ESI) calc’d for [Ci2H7ClFN202]”([M-H]”): m/z 265.0, found 265.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; BRUICK, Richard, K.; CALDWELL, Charles, G.; FRANTZ, Doug, E.; GARDNER, Kevin, H.; MACMILLAN, John, B.; SCHEUERMANN, Thomas, H.; TAMBAR, Uttam, K.; WO2014/78479; (2014); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4863-91-6, Name is 3-Chloro-5-fluoroaniline, 4863-91-6, belongs to chlorides-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.

To a cooled (0 C) solution of 3-chloro-5-fluoroaniline (5.0 g, 33 mmol) in MeCN (50 ml) was added a suspension of N-bromosuccinimide (5.9 g, 33 mmol) in MeCN (10 ml). After being stirred for 2 h at RT the reaction was quenched by adding 10 % NaHS03 (50 ml). The mixture was concentrated to about half of the volume, diluted with water (50 ml) and extracted with EtOAc (3×50 ml). Combined organic phases were dried over Na2S04 and evaporated to give crude product, which was purified by CombiFlash (column: silica, eluent: 0-100 % EtOAc in heptane) to yield 5.5 g (74 %) of the title compound. -NMR (400MHz; d6-DMSO): delta 5.88 (bs, 2H), 6.45 (dd, IH), 6.64 (m, IH).

Statistics shows that 3-Chloro-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 4863-91-6.

Reference:
Patent; ORION CORPORATION; WOHLFAHRT, Gerd; TOeRMAeKANGAS, Olli; SALO, Harri; HOeGLUNG, Lisa; KARJALAINEN, Arja; KNUUTTILA, Pia; HOLM, Patrick; RASKU, Sirpa; VESALAINEN, Anniina; WO2011/51540; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics