Category: 327-51-5

Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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. category: bromides-buliding-blocks

A solution of 1,4-dibromo-2,5-difluorobenzene (640 mg, 2.35 mmol) in dry diethyl ether (10 mL) cooled in a dry ice-acetone bath was treated dropwise with 2.5 M n-butyllithium in hexanes (1.04 mL, 2.59 mmol). The resulting solution was stirred at -78 C. for 30 min, then was treated with a piece of dry ice. The cooling bath was removed after 5 min and the mixture was stirred for another 30 min while warming to room temperature. The mixture was diluted with EtOAc and water. The organic phase was separated and washed twice with saturated aqueous NaHCO3. The combined aqueous phases were acidified with 1 M aqueous HCl, extracted twice with DCM, and the combined organic phases were dried and concentrated to give 4-bromo-2,5-difluorobenzoic acid as a white solid (297 mg, 53% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-51-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-51-5, 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 327-51-5 as follows.

1,4-Dibromo-2,5-difluorobenzene, 4-methoxycarbonylphenylboronic acid, potassium carbonate and tetrakis (triphenylphosphine) palladium were placed in a reaction In the reactor, and ethylene glycol dimethyl ether was added to the reactor, Then under the protection of nitrogen at 85 C for 36h after the first reaction A reaction solution, after the first reaction solution is cooled, The first reaction solution was poured into water and extracted with dichloromethane, and then ethylene glycol dimethyl ether was removed, The remaining material after pumping away ethylene glycol dimethyl ether, separated and purified by silica gel column chromatography to give To the intermediate product 2 ‘, 5′-difluoro- [1,1’: 4 ‘, 1 “-terphenyl] -4,4” -dimethyl ester;

According to the analysis of related databases, 327-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong University of Technology; He Jun; Huang Jian; Cao Peng; He Yonghe; Huang Jiahong; (22 pag.)CN105542751; (2017); B;,
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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 327-51-5

under a nitrogen atmosphere, to a 500ml reaction vessel 2,3-dibromo-thiophene (Wako Pure Chemical Industries, Ltd.) added to 15g and THF160ml did. This solution under ice-cooling ethyl magnesium chloride (Sigma-Aldrich, 2.0M) was added to THF solution 32ml (63mmol) of, and stirred for 10 minutes at the same temperature, 3-bromothiophene-2-magnesium chloride (3-halo thiophene-2-magnesium halide) was prepared. It added another 1l reaction vessel to zinc chloride (Wako Pure Chemical Industries, Ltd.) 10g (73mmol) and THF100ml, was a fine white slurry was stirred under ice-cooling. Then 3-bromo-2-magnesium chloride in an ice-cold solution of the (water bath temperature 10 C) was transferred to the zinc chloride solution, and the mixture was stirred for 30 minutes. Further the temperature was raised to room temperature, stirred for 10 minutes, 3-bromo-2-zinc chloride (3-halo-2-zinc derivative) was prepared. To this mixture 1,4-dibromo-2,5-difluorobenzene (Wako Pure Chemical) 5.5 g (20 mmol), catalyst as tetrakis (triphenylphosphine) palladium (Tokyo Kasei Kogyo) 350 mg (0.30 mmol) (1 , it was added 1.5 mol%) on the 4-dibromo-2,5-difluorobenzene. After carrying out 25 hours cross-coupling reaction at 50 C, the reaction by the addition of water-cooled vessel 1N hydrochloric acid 90ml stopped. It was extracted with toluene and the organic phase was washed with brine, and dried with anhydrous sodium sulfate. Concentrated in vacuo, and filtered resulting residue in a small amount of silica gel, concentrated crystal was further washed with hexane. Heptane / toluene = purified by recrystallization from 2/1, to give a pale yellow solid 5.3g of 1,4-bis (3-bromo-2-thienyl) -2,5-difluoro-benzene (61% yield).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tosoh Corporation; Ueda, Saori; Watanabe, Masato; (7 pag.)JP2016/74626; (2016); A;,
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 327-51-5 as follows. COA of Formula: C6H2Br2F2

Compound A-14 (24.6 g, 74 mmol), 1, 4-dibromo-2, 5-difluorobenzene (20 g, 74 mmol), and a 2 M aqueous solution of Na2CO3 (75 mL, 150 mmol), DME (150 mL), toluene (150 mL), and Pd [PPh3]4 (4.3 g, 3.7 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (100 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtrated and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 21 g in 60% yield. FD-MS C24H13BrF2N2O2: theoretical value 479, observed value 479

According to the analysis of related databases, 327-51-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2301921; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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 1,4-Dibromo-2,5-difluorobenzene

1,4-Dibromo-2,5-difluorobenzene (51.2 g, 188 mmol) was dissolved in 1,2-diethoxyethane (400 ml), and a 2.5 M n-butyllithium/ hexane solution (76.0 ml, 190 mmol) was slowly added dropwise thereto at -78 C. in the presence of nitrogen gas. [0674] After the reaction solution was stirred at -78 C. for 30 minutes, dry ice was added thereto, followed by stirring for further 30 minutes. After the temperature was gradually raised to room temperature, water (200 ml) was added to the reaction liquid. The reaction liquid was diluted with ethyl acetate, and washed with a 10% aqueous sodium carbonate solution (200 ml¡Á2). Then, the obtained aqueous layers were combined, and made acidic by adjustment with 1 N hydrochloric acid. The precipitated yellow solid was filtered and dried to obtain the title compound (30.0 g, 67%). [0675] 1H NMR (DMSO-d6, 400 MHz): delta 7.90-7.87 (m, 1H), 7.79-7.75 (m, 1H).; MS (ESI) m/z 191 (M+H-44)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-51-5, its application will become more common.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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. category: bromides-buliding-blocks

Add 1,4-dibromo-2,5-difluorobenzene (1.09 g, 4 mmol), phenylboronic acid (1.21 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (468 mg, 0.4 mmol) THF (50 mL) and aqueous potassium carbonate (1M, 20 mL) were then evaporated and then th After cooling to room temperature, the layers were separated. The aqueous phase was extracted with dichloromethane (3¡Á50 mL). The residue was purified by silica gel column was using dichloromethane: hexane (1: 5) as eluent to give the product as a white solid (0.82g, 77.1%);

The synthetic route of 1,4-Dibromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Normal University; Ren Xiuhui; Zhu Fucheng; Zhang Xi; Geng Yan; (23 pag.)CN110003179; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 327-51-5, These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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 1 , 4-dibromobenzene (4.4 g, 16.3 mmol) , 2-(tributylstannyl)pyrimidine (3.0 g, 8.13 mmol), copper (I) iodide (154 mg, 0.81 mmol) in toluene (50 ml) were purged with nitrogen for 15 min.Tetrakis(thphenylphosphine)palladium(0) (939 mg, 0.81 mmol) was added and the mixture was stirred at 110 C in a sealed-tube for 1 day. The mixture was cooled to r.t. and was diluted with water and ethyl acetate. Layers were separated. The separated organic layer was dried (MgSO4), filtered and solvents were removed in vacuum. Column purification [Hexanes – Ethyl acetate, 2:1 (v/v)] gave bromide 2AD (1.09 g, 50%) as white solid.

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/156739; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 327-51-5,Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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 1,4-dibromo-2,5-difluorobenzene (i-6a) (27.0 g, 100 mmol) in THF(500 ml) was added n-BuLi (60 ml, 2M) dropwise at -78C and the reaction mixture was kept stirring for 3h. Then excess dry ice was added into the reaction mixure portwise over 0.5 h. The reaction mixture wasquenched with 300 ml water and extracted with EA (100 mlx 3). The aqueous solution was acidified with HC1 (2M), extracted with EA (150 mlx3), and the organic layer was dried and concentrated. The crude material was purified by chromatography column (EA:PE = 1:10) to afford 18.24 g product (76%). LCMS (ESI) calc?d [M+H]: 237.00, found: 237.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dibromo-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan; WO2014/28589; (2014); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 327-51-5, A common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, molecular formula is C6H2Br2F2, 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.

(1380) [00444] Into a 50-mL round-bottom flask that was purged and maintained under an inert atmosphere of nitrogen was added 1 ,4-dibromo-2,5-difiuorobenzene (1.50 g, 5.52 mmol), tert- butyl 4-(tetramethyl-l,3,2-dioxaborolan-2-yl)-l,2,3,6-tetrahydropyridine-l-carboxylate (1.88 g, 6.06 mmol), potassium carbonate (2.28 g, 16.5 mmol), Pd(dppf)Cb’CH2Cl2 (400 mg, 0.49 mmol), DMF (20 mL) and H2O (2 mL). The reaction mixture was stirred for 2 h at 50 C and then cooled and quenched with water (20 mL). The resulting solution was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL). The organic layer was then concentrated in vacuo. The resulting crude product was purified by FCC eiuting with petroleum ether/ethyl acetate (5: 1) to afford fer/-butyl 4-(4-bromo- 2,5-difluorophenyl)-3,6-dihydropyridine-l(2 )-carboxylate (1.5 g, 73%). H-NMR (300 M ( DO delta ppm 7.21-7.29 (m, 1H), 6.93-7.08 (m, 1H), 5.81-5.61 (m, 1H), 4.01-4.14 (m, 2H), 3.62 (t, J – 5,7 Hz, 2H), 2.48-2.51 (m, 2H), 1 ,50 (s, 9H).

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORMA THERAPEUTICS, INC.; GUERIN, David Joseph; BAIR, Kenneth W.; CARAVELLA, Justin A.; IOANNIDIS, Stephanos; LANCIA JR., David R.; LI, Hongbin; MISCHKE, Steven; NG, Pui Yee; RICHARD, David; SCHILLER, Shawn E. R.; SHELEKHIN, Tatiana; WANG, Zhongguo; (365 pag.)WO2017/139778; (2017); 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H2Br2F2

Synthesis of H2 (p-F2-bdp). H2(p-F2-bdp) was prepared via a Suzuki-Miyaura coupling as generally depicted in Scheme 3. Specifically, 1,4-dibromo-2,5-difluorobenzene (2.18 g, 8.0 mmol, 1.0 equiv), 1-(2-tetrahydropyranyl)-1H-pyrazole-4-boronic acid pinacol ester (5.56 g, 20.0 mmol, 2.5 equiv), and K3PO4 (8.48 g, 40 mmol, 5 equiv) were suspended in toluene (16 mL) in a 40-mL glass scintillation vial with a magnetic stir bar and sparged with Ar for 10 minutes. XPhos Pd G2 (1.26 g, 1.6 mmol, 0.2 equiv) was added quickly in air, and vial was briefly purged with Ar, sealed with a PTFE-lined cap, and heated to 110 C. while stirring for 2 days. Upon completion, the reaction mixture was cooled to room temperature, concentrated under reduced pressure, and diluted with 250 mL of diethyl ether. The ether layer was washed 5 times with 250 mL of saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated under reduced pressure to yield a yellow oil, which was used in the subsequent reaction without additional purification. The crude ligand was dissolved in 60 mL of methanol in a 250-mL round-bottom flask with a magnetic stir bar, 12 mL of concentrated aqueous HCl was added, and the reaction mixture was stirred at 50 C. for 2 h, during which time a white precipitate formed. The reaction mixture was filtered, and the filtrate was suspended in water and neutralized with NaHCO3. The precipitate was again isolated by filtration, washed with water, and dried in vacuo to yield H2(p-F2-bdp) (0.86 g, 3.5 mmol, 44%) as a beige powder. 1H NMR (400 MHz, DMSO-d6): delta 8.11 (s, 4H), 7.68 (t, J=9.3 Hz, 2H) ppm; 13C NMR (101 MHz, DMSO-d6): delta 156.06, 153.68, 132.40, 119.33-119.81 (m), 118.58-118.14 (m), 114.60-113.78 (m) ppm; 19F NMR (400 MHz, DMSO-d6): delta -119.78 (t, J=9.3 Hz) ppm. Note that the 1H NMR signals from the hydrogen atoms bonded to the pyrazole nitrogen atoms are too broad to be visible. Anal. Calcd. for C12H8F2N4: C, 58.54, H, 3.27, N, 22.75; found: C, 57.72, H, 3.35, N, 21.82. IR: 3139 (m), 3076 (w), 2966 (m), 2938 (m), 2850 (m), 1589 (m), 1539 (w), 1490 (m), 1435 (w), 1374 (m), 1350 (w), 1273 (m), 1241 (w), 1155 (s), 1041 (m), 963 (s), 867 (s), 818 (m), 780 (s), 698 (m), 668 (w), 605 (s), 549 (w), 531 (w), 512 (w), 482 (w), 472 (w), 460 (m) cm-1.

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of California; Long, Jeffrey R.; Mason, Jarad A.; Taylor, Mercedes K.; Oktawiec, Julia; (70 pag.)US2018/297010; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary