Category: 5905-69-1

Application of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 346: Ethyl (2E)-3-{1-[4-(difluoromethoxy)phenyl]-3-(2-phenylethyl)-1H-indol-5-yl}propenoate; To a solution of the compound obtained at Example 141 (200 mg) in n-butyl acetate (15 ml) were added 1-bromo-4-(difluoromethoxy)benzene (281 mg), palladium acetate (28 mg), 2-(di-tert-butylphosphino)biphenyl (75 mg) and tripotassium phosphate (535 mg), and the mixture was heated and stirred at 120C for 12 hours. The reaction mixture was cooled to room temperature, then the insolubles were filtered off, the filtrate was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:11) to afford the above-identified compound (227 mg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(difluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP2141148; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 5905-69-1, 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 5905-69-1 as follows.

A. 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolaneA mixture of commercially available l-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.2g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.18 g, 0.22 mmol) in DMF (15 mL) was stirred under nitrogen at 90 0C for 1 hour. Diluted with DCM, washed with water, sat. NaHCC^, brine, dried (MgSC^), and concentrated.The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 13A (1.12 g, 3.32 mmol, 74.0 % yield) as a brown oil.

According to the analysis of related databases, 5905-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; WASHBURN, William, N.; HERNANDEZ, Andres, S.; ROBL, Jeffrey, A.; NGU, Khehyong; WANG, Zhenghua; WO2010/104830; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5905-69-1, These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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.

(Reference Example 71) Ethyl 1-[4-(difluoromethoxy)phenyl]piperidine-4-carboxylate[0521] Sodium tert-butoxide (2.29 g, 23.8 mmol), palladium(II) acetate (428 mg, 1.91 mmol), and tri-tert-butylphosphine (370 muL, 1.52 mmol) were added to a solution of ethyl piperidine-4-carboxylate (3.52 mL, 22.9 mmol) and 1-bromo-4-(difluoromethoxy)benzene (4.25 g, 19.1 mmol) in toluene (122 mL), and the mixture was stirred at 80C for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 100/0 – 90/10] to obtain the title compound (3.17 g, yield: 56%). [0523] 1H-NMR (400 MHz, CDCl3) delta: 7.07-7.00 (2H, m), 6.95-6.87 (2H, m), 6.41 (1H, t, J = 75 Hz), 4.16 (2H, q, J = 7 Hz), 3.61-3.55 (2H, m), 2.84-2.73 (2H, m), 2.47-2.39 (1H, m), 2.08-1.99 (2H, m), 1.95-1.83 (2H, m), 1.27 (3H, t, J = 7 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5905-69-1.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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: 1-Bromo-4-(difluoromethoxy)benzene

A mixture of 1-bromo-4-(difluoromethoxy)benzene (230 mg, 1.05 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (402 mg, 1.58 mmol), PdCl2 (dppf) (20 mg), and Cs2CO3 (682 mg, 2.1 mmol) in dioxane was sealed in a microwave reaction cube and reacted at 180 C. for 2 hours in a microwave reactor. Then it was purified by flash column chromatography (PE/EA) to give the crude compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5905-69-1, its application will become more common.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; Su, Wei-Guo; Deng, Wei; Ji, Jianguo; US2014/121200; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Bromo-4-(difluoromethoxy)benzene 6 (2.23 g, 10 mmol), potassium acetate (30.0 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (11.0 mmol) and Pd(PPh3)4 (0.5 mmol) are added to a 40-mL Schlenk flask equipped with a stir bar. The flask is evacuated and backfilled with nitrogen several times. 1,4-Dioxane (10 mL) is added by syringe. The Schlenk flask is sealed and heated at 1500C for 20 min in a microwave oven. After the reaction is complete, the solvent is removed under vacuum. The residue is dissolved in DCM (200 mL) and washed with water. The organic phase is dried with anhydrous Na2SO4, filtered and concentrated to yield a crude product. Purification by silica gel column chromatography (EtOAc : hexanes, gradient from 0% to 20%) affords 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 7. 1H NMR (400MHz, CDCl3) delta 7.74 (d, J = 8.4 Hz, 2H), 7.02 (d, J = 8.4 Hz, 2H), 6.48 (t, J = 73.6 Hz, IH), 1.27 (s, 12H). MS (m/z) (M+l)+: 271.1.

The synthetic route of 1-Bromo-4-(difluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2009/26276; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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.

Copper iodide (54 mg, 0.283 mmol) and Tetrakis(triphenylphosphine) palladium (105 mg, 0.091 mmol) were added. Lastly 1-bromo-4-(difluoromethoxy)benzene (0.750 g, 3.36 mmol) was added, the vial was covered with a teflon septa, an aluminum cap was crimped in place, and the assembly was set on a Biotage Emrys microwave instrument to irradiate at 80 C. for 30 minutes. The crude reaction was diluted with diethylether, washed with saturated ammonium chloride, and purified via column chromatography on a Yamazen W-Prep 2XY using 25% EtOAc in hexanes. Concentration by rotary evaporation afforded 500 mg of oil (96%); 1H NMR (400 MHz, DMSO-d6) delta ppm 3.03 (t, J=4.6 Hz, 4H) 3.73 (t, J=4.6 Hz, 4H) 7.13-7.14 (m, 1H) 7.16 (d, J=2.6 Hz, 1H) 7.17-7.19 (m, 2H) 7.22 (d, J=8.8 Hz, 2H) 7.24 (t, J=73.8 Hz, 1H) 7.60 (d, J=8.8 Hz, 2H); MS (ES) m/z 348.2 [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 1-Bromo-4-(difluoromethoxy)benzene, its application will become more common.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, 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. Quality Control of 1-Bromo-4-(difluoromethoxy)benzene

Step 4) 1-difluoromethoxy-4-{3-[3-(2-methoxy-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-methoxy-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (1.00 g, 2.70 mmol) was dissolved in THF (5 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (5 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (1.20 gm, 5.38 mmol), copper iodide (70 mg, 0.262 mmol), tetrakis(triphenylphosphine)palladium (140 mg, 0.120 mmol) and triethylamine (5.8 g, 98 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%-10% EtOAc in hexanes) afforded an oil 882 mg (46%). This material was used in next step without further characterization.

The synthetic route of 1-Bromo-4-(difluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 5905-69-1,Some common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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.

Step 3. Synthesis of ethyl 5-(4-(difluoromethoxy)phenyl)isoxazole-3- carboxylate [1.2.11c] 1.2.11c A vial was charged with 1.2.11 b (0.76 g, 1.77 mmol, 1.0 equiv) and 1-bromo-4- uoromethoxy) benzene (0.5 g, 2.13 mmol, 1.2 equiv) were dissolved in 1 ,4-dioxane (10 ml_). Pd(PPh3)2CI2 (0.062 g, 0.085 mmol, 0.05 equiv) was added and the reaction mixture was stirred at 130 C for 2 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (0-10 % EtOAc in Hexane) to afford product 1.2.11c (0.6 g, 94 % yield). LCMS (m/z): 284.2 [M+H]. 1H NMR (400 MHz, CDCI3) delta 7.89 – 7.81 (m, 2H), 7.28 – 7.24 (m, 2H), 6.93 (s, 1 H), 6.4 – 6.9 (3s, 1 H), 4.19 (q, J = 7.1 Hz, 2H), 1.31 – 1.29 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-(difluoromethoxy)benzene, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Jiping; KARUR, Subramanian; MADERA, Ann Marie; PECCHI, Sabina; SWEENEY, Zachary Kevin; TJANDRA, Meiliana; YIFRU, Aregahegn; WO2014/160649; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 5905-69-1, A common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, molecular formula is C7H5BrF2O, 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 bromophenol derivative AM (2.0 g, 8.97 mmol) in 1,4-dioxane (40 mL) were added bis(pinacolato)diboron (2.28 g, 8.97 mmol) and KOAc (2.64 g, 26.90 mmol) at RT under inert atmosphere, and the mixture was degassed for 20 min by purging with argon. To this solution, Pd(dppf)2Cl2 (0.33 g, 0.45 mmol) was added, and the mixture was degassed for a further 10 min. The reaction mixture was then heated to 80 C. and stirred for 3 h at this temperature. Progress of the reaction was monitored by TLC. The reaction mixture was then cooled to RT and diluted with EtOAc (30 mL). The resultant solution was filtered through a Celite pad, and the filtrate was then concentrated in vacuo. The crude compound was purified by silica gel column chromatography (eluting with 5-10% EtOAc gradient in hexanes) to afford AN (1.72 g, 6.37 mmol, 71%). 1H NMR (500 MHz, CDCl3): delta 7.81 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.5 Hz, 2H), 6.54 (t, JF-H=74.0 Hz, 1H), 1.34 (s, 12H).

The synthetic route of 5905-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; US2012/329802; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 346: Ethyl (2E)-3-{1-[4-(difluoromethoxy)phenyl]-3-(2-phenylethyl)-1H-indol-5-yl}propenoate; To a solution of the compound obtained at Example 141 (200 mg) in n-butyl acetate (15 ml) were added 1-bromo-4-(difluoromethoxy)benzene (281 mg), palladium acetate (28 mg), 2-(di-tert-butylphosphino)biphenyl (75 mg) and tripotassium phosphate (535 mg), and the mixture was heated and stirred at 120C for 12 hours. The reaction mixture was cooled to room temperature, then the insolubles were filtered off, the filtrate was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:11) to afford the above-identified compound (227 mg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(difluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP2141148; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem