Category: 179897-90-6

Synthetic Route of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

EXAMPLE 185 6-(3-Bromo-2-chloro-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 285, structure 4 of Scheme II, where R1 =3-bromo-2-chloro-5-fluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (143.3 mg, 0.45 mmol) and 1-chloro-2,6-dibromo-4-fluorobenzene (129.9 mg, 0.45 mmol). The crude material was purified by flash column chromatography (50 mL silica, hexane) followed by reverse phase preparatory TLC (1000 mL ODS, 80% methanol/water) to afford 4.3 mg (3%) of Compound 285. Data for Compound 285: 1 H NMR (400 MHz, acetone-d6) 7.50 (dd, J=7.8, 3.0, 1H), 7.19 (dd, J=9.2, 3.0, 1H), 7.10 (d, J=2.0, 1H), 7.03 (dd, J=8.1, 2.0, 1H), 6.55 (d, J=8.3, 1H), 5.61 (s, 1H), 5.37 (s, 1H), 1.97 (s, 3H), 1.29 (s, 6H).

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; Ligand Pharmaceuticals Incorporated; US5688810; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 179897-90-6, 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. 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Step 1. Preparation of 3-bromo-2-chloro-5-fluoroaniline To a sealable glass tube was charged 1,3-dibromo-2-chloro-5-fluorobenzene (12.52 g, 43.4 mmol), benzophenone imine (8.26 g, 45.6 mmol), sodium tert-butoxide (6.26 g, 65.1 mmol), and toluene (100 mL). The resulting mixture was thoroughly sparged with Argon, followed by the addition of Pd2(dba)3 (0.398 g, 0.434 mmol) and (S)-BINAP (0.81 g, 1.3 mmol), and follow by another Argon sparge. The reaction tube was sealed and heated to 85 C. in an oil bath and maintained overnight. The reaction was allowed to cool to room temperature and quenched with water (20 mL). The resulting layers were partitioned and separated. The organic phase was concentrated and assayed to be a mixture of mono- and bis-aminated products (~4:1 by HPLC area at 220 nm). The residue was dissolved in THF (70 mL), treated with aqueous 3.0 M HCl (20 mL) at room temperature for 1 hour and basified with saturated aqueous Na2CO3 solution (40 mL). The reaction mixture was allowed to partition and the layers were separated. The organic portion was separated, washed with brine, concentrated and the resulting residue was purified by flash chromatography (SiO2, 0-15% EtOAc in heptane) and 3-bromo-2-chloro-5-fluoroaniline was obtained as a light yellow solid (6.82 g, 30.4 mmol): LCMS(m/z): not ionized (MH+), tR=0.95 minute; 1H NMR (CDCl3, 300 MHz) delta 4.32 (br s, 2H), 6.44 (dd, J=9.8, 2.8 Hz, 1H), 6.77 (dd, J=7.9, 2.6 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 1,3-Dibromo-2-chloro-5-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Costales, Abran Q.; Huang, Shenlin; Jin, Jeff (Xianming); Liu, Zuosheng; Pecchi, Sabina; Poon, Daniel; Tellew, John; US2011/52578; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

DMF (dimethylformaldehyde)To a solution of 1,3-dibromo-2-chloro-5-fluorobenzene (23.0 g, 79.8 mmol)And di-tert-butylphenylamine (24.3 g, 144 mmol)And cesium carbonate (84.4 g, 239 mmol) were charged, and the mixture was heated to 140 C and reacted for 40 hours.After cooling to room temperature, the mixture was extracted with EA, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.This was subjected to column chromatography with EA: Hx to obtain 12.0 g (Yield = 34%) of [Intermediate 12-1].

The synthetic route of 179897-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; Gu Gi-dong; Yoon Jeong-min; Kim Gong-gyeom; Huh Nan-seul-a; Lee Gi-gon; Keum Su-jeong; (52 pag.)KR2018/112721; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 179897-90-6 as follows. Quality Control of 1,3-Dibromo-2-chloro-5-fluorobenzene

[00185] Intermediate. 3-Bromo-2-chloro-5-fluoroaniline[00186] Step 1. 3-bromo-2-chloro-N-(diphenylmethylene)-5-fluoroaniline. A mixture of 2,6-dibromo-4-fluoro-l-chlorobenzene (865 mg, 3 mmol), benzophenone imine (0.61 ml, 3.6 mmol), Pd2(dba)3 (137 mg, 0.15 mmol), sodium t-butoxide (432 mg, 4.5 mmol), (S)-BINAP (280 mg, 0.45 mmol), and toluene (30 ml) was heated at 80 0C for 16 h. The mixture was extracted with ethyl acetate and the combined organic phase washed with brine. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by silica gel flash chromatography (40:1 to 20:1 hexanes/ethyl acetate eluant) to provide the title compound as a powder. MS m/z 388.9 (M + 1).

According to the analysis of related databases, 179897-90-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; NOVARTIS AG; HUANG, Shenlin; JIN, Xianming; LIU, Zuosheng; POON, Daniel; TELLEW, John; WAN, Yongqin; WANG, Xing; XIE, Yongping; WO2011/25927; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, 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 179897-90-6, Safety of 1,3-Dibromo-2-chloro-5-fluorobenzene

l,3-Dibromo-2-chloro-5-fluorobenzene (400 mg, 1.39 mmol) dissolved in toluene (4 mL) and 2- methyltetrahydrofuran (1 mL) was treated with the triisopropyl borate (390 pL, 1.69 mmol). The mixture was cooled to -78 C in a dry ice/acetone bath and then n-butyllithium (2.5 M in hexanes, 680 pL, 1.70 mmol) was added slowly dropwise. The mixture was maintained at -78 C for 1 h and then slowly allowed to warm to room temperature. After stirring for 1 h, the reaction mixture was quenched by adding 1N HC1 solution, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and purified by ISCO silica gel chromatography to give (3-bromo-2-chloro-5-fluorophenyl)boronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 179897-90-6, A common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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 150 mL of DMF (dimethylformaldehyde), 1,3-dibromo-2-chloro-5-fluorobenzene (23.0 g, 79.8 mmol), dimethylamine (24.3 g, 144 mmol) and cesium carbonate (84.4 g, 239 mmol) were added thereto, and the mixture was heated to 140 C and reacted for 40 hours. After cooling to room temperature, the mixture was extracted with EA, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. This was subjected to column chromatography with EA: Hx to obtain 12.0 g (Yield = 34%) of [Intermediate 7-1].

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; LG Chem, Ltd.; Gu Gi-dong; Lee Gi-gon; Keum Su-jeong; Yoon Jeong-min; Lee Hyeong-jin; Kim Gong-gyeom; (57 pag.)KR2018/112722; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, 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 179897-90-6, Formula: C6H2Br2ClF

EXAMPLE 185 6-(3-Bromo-2-chloro-5-fluorophenyl)-1,2-dihydro-2,2A-trimethylquinoline (Compound 285, structure 4 of Scheme II, where R1 =3-bromo-2-chloro-5-fluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (143.3 mg, 0.45 mmol) and 1-chloro-2,6-dibromo-4-fluorobenzene (129.9 mg, 0.45 mmol). The crude material was purified by flash column chromatography (50 mL silica, hexane) followed by reverse phase preparatory TLC (1000 mL ODS, 80% methanol/water) to afford 4.3 mg (3%) of Compound 285. Data for Compound 285: 1 H NMR (400 MHz, acetone-d6) 7.50 (dd, J=7.8, 3.0, 1 H), 7.19 (dd, J=9.2, 3.0, 1 H), 7.10 (d, J=2.0, 1 H), 7.03 (dd, J=8.1, 2.0, 1 H), 6.55 (d, J=8.3, 1 H), 5.61 (s, 1 H), 5.37 (s, 1 H), 1.97 (s, 3 H), 1.29 (s, 6 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5696130; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6, The chemical industry reduces the impact on the environment during synthesis 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, I believe this compound will play a more active role in future production and life.

A scalable tube was charged with 1,3-dibromo-2-chloro-5-fluoroben;jene(1.0, 12.52 g, 43.4 mmoi), benzophepsilon?one iniine(H.26 g, 45.6 mmoi), sodium tert-Bupsilontoxide(8.26 g, 65.1 mmoi), and loluene(100 ml). The resulting mixture was thoroughly sparged with Argon, then followed by addition of Pd2(dba)Lambda(Q398 g, 0.434 mmoi) and (S)«B.NAP(0.81 1 g, 1.3 mmoi) and Argon sparge was repealed. Reaction was sealed and heated overnight to 85C using an oil bath. Reaction mixture was cooled down to ambient temperature, quenched with water(20ml). Toluene layer was isolated, concentrated and residue was a mixture of mono-coupling product and his-coupUng byproduct with ratio -4:1 by fc:JPLC area at 220 nm. Residue was dissolved in TlIF (70 ml), treated with 3M MCI (20 ml) at room temperature for 1 hour and basified with sat. -Na2CO3 (40 ml). THF layer was separated, washed with brine, concentrated and residue was purified by flash chromatography on silica gel and 12 was obtained as a light yellow solid( 6.32 g, 30.4 mmot, yield 70%.LC/MS: (M+HJ=ncrt ionized, f« – 0.9 min);1H NMR(CDCl3, 300 MHz) 6 ppm 4.32 (s, 2 H), 6.44(dd, J, <;? 9.82 Hz, J2 *2.78 Hz, 1 H), 6.77<;dd, J1« 7.91 Hz, J2 -- 2.64 Hz, I H). 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, 1,3-Dibromo-2-chloro-5-fluorobenzene, other downstream synthetic routes, hurry up and to see. Reference:
Patent; NOVARTIS AG; HUANG, Zilin; SENDZIK, Martin; WO2010/100127; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 179897-90-6,Some common heterocyclic compound, 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, molecular formula is C6H2Br2ClF, 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 round bottom flask under nitrogen fitted with a stir bar was added 1- chloro-2,6-dibromo-4-fluorobenzene (14.36 g, 49.8 mmol), pivalamide (5.04 g, 49.8 mmol), cesium carbonate (21.09 g, 64.7 mmol) and dioxane (250 mL). The reaction mixture was sparged with nitrogen and Pd(dba)2 (1.43 g, 2.490 mmol) and 5-bis(diphenylphosphino)-9,9- dimethylxanthene (XANTPHOS, 2.02 g, 3.49 mmol) were added. The reaction was then sealed and heated in an oil bath at 70 C for 18 h. The reaction was allowed to cool to r.t and was partitioned between a saturated aqueous solution of NH4C1 and EtOAc. The layers were separated and the aqueous portion was extracted with EtOAc (2 X). The combined organic portions were washed with water, brine, dried (Na2S04), filtered, concentrated, and adsorbed onto silica gel. Purification by flash chromatography on silica gel using an EtO Ac- heptane (1-20%) elution gradient afforded N- (3-bromo-2-chloro-5-fluorphenyl)pivalamide (1 1.0 g, 33.8 mmol, 68 %) as a white crystalline solid. LCMS (m/z): 309.9 (MH+), tR = 1.1 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Dibromo-2-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; NOVARTIS AG; MADERA, Ann Marie; POON, Daniel; SMITH, Aaron; WO2011/161216; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H2Br2ClF

EXAMPLE 185 6-(3-Bromo-2-chloro-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 285, Structure 4 of Scheme II, where R1 =3-bromo-2-chloro-5-fluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (143.3 mg, 0.45 mmol) and 1-chloro-2,6-dibromo-4-fluorobenzene (129.9 mg, 0.45 mmol). The crude material was purified by flash column chromatography (50 mL silica, hexane) followed by reverse phase preparatory TLC (1000 mL ODS, 80% methanol/water) to afford 4.3 mg (3%) of Compound 285. Data for Compound 285: 1 H NMR (400 MHz, acetone-d6) 7.50 (dd, J=7.8, 3.0, 1 H), 7.19 (dd, J=9.2, 3.0, 1 H), 7.10 (d, J=2.0, 1 H), 7.03 (dd, J=8.1, 2.0, 1 H), 6.55 (d, J=8.3, 1 H), 5.61 (s, 1 H), 5.37 (s, 1 H), 1.97 (s, 3 H), 1.29 (s, 6 H).

The synthetic route of 179897-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics