Category: 128140-82-9

Application of 128140-82-9, A common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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.

Step 7) 4-[5-(4-Difluoromethoxy-phenylethynyl)-2-fluoro-phenyl]-butyronitrile To a solution of 1-Difluoromethoxy-4-iodo-benzene (0.21 g, 0.79 mmol) in DMF (3.5 ml) were added TEA (0.55 mL, 57.4 mmol) and 4-(5-Ethynyl-2-fluoro-phenyl)-butyronitrile (0.48 g, 0.79 mmol). The reaction was degassed by bubbling argon through it for 5 min and then dichlorbis(triphenylphospine)palladium (0.0.28 g, 0.04 mmol), and copper iodide (0.008 g, 0.57 mmol) were added simultaneously. The reaction mixture was heated at 65 C. for 15 min. cooled and quenched with 0.1 N HCl (10 ml). The aqueous layer was extracted with Et2O (3*10 ml). The combined organic extracts were washed with brine (25 ml), dried (MgSO4), and concentrated. The crude material was purified by silica gel chromatography (10-20% Ethyl acetate/Petroleum Ether) to afford the titled compound (0.235 g, 90%) as a brown oil that solidified on standing, and was identified by NMR and mass spectral analyses. MS (EI+): 329 (M+).

The synthetic route of 128140-82-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 128140-82-9,Some common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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 110; Preparation of 1-(difluoromethoxy)-4-ethynylbenzene; A solution of 1-(difluoromethoxy)-4-iodobenzene (12.7 g, 50 mmol) in triethylamine is treated with tetrakis(triphenylphosphine)palladium (4.0 g, 3.5 mmol), copper iodide (925 mg, 4.85 mmol), and a solution of ethynyl(trimethyl)silane (6.9 mL, 50 mmol) in acetonitrile at room temperature, stirred for 1 h at 60 C. and concentrated in vacuo. The resultant residue was dissolved in Et2O and filtered. The filtrate was concentrated and the concentrate was purified by chromatography (silica gel, EtOAc/hexane: 5/95) to give {[4-(difluoromethoxy)phenyl]ethynyl}(trimethyl)silane (11.5 g, 96%) as an oil. A solution of {[4-(difluoromethoxy)phenyl]ethynyl}(trimethyl)silane (10.0 g, 41.7 mmol) in MeOH/CH2Cl2 (1/1) was treated with cesium carbonate (16.3 g, 50 mmol) at room temperature, stirred for 1.5 h, diluted with CH2Cl2 and filtered through a pad of silica gel. The filtrate was concentrated to dryness to give the title compound (6.8 g, 97%) as an oil. MS (+) EI: 168.

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

Reference:
Patent; Wyeth; US2007/4730; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, belongs to iodides-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 128140-82-9, Quality Control of 1-(Difluoromethoxy)-4-iodobenzene

Step a) 1-(Difluoromethoxy)-4-(phenylethynyl)benzene Into a mixture of ethynylbenzene (1.9 g, 18.5 mmol), 1-(difluoromethoxy)-4-iodobenzene (5 g, 18.5 mmol), N,N-dimethylformamide (35 mL), and triethylamine (12.8 mL, 92.6 mmol) was introduced anhydrous argon for 5 minutes. Then, copper(I) iodide (1.85 mmol, 351 mg) and dichlorobis(triphenylphosphine)palladium(II) (1.11, 0.71 g) were added into the mixture and the new mixture was stirred at 60 C. for 3 hours. The mixture cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were dried over MgSO4. Evaporation and purification on silica gel (ISCO) using hexanes/EtOAc (100/1) as the eluding solvent, gave 1-(difluoromethoxy)-4-(phenylethynyl)benzene as a clear oil (3.45 g, 76% yield). MS m/e M+244; 1H NMR (400 MHz, DMSO-d6) delta 7.2 (d, J=8.78 Hz, 2H), 7.28-7.45 (m, 4H), 7.5-7.55 (m, 2H), 7.6 (d, J=7.78 Hz, 2H).

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-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 128140-82-9

Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol A solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260.

According to the analysis of related databases, 128140-82-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2007/72925; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 128140-82-9, The chemical industry reduces the impact on the environment during synthesis 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, I believe this compound will play a more active role in future production and life.

Step 1) 1-((4-(Difluoromethoxy)phenyl)ethynyl)-3-methylbenzene To a solution of 3-bromophenylacetylene (2.5 g, 21.5 mmol), TEA (9.57 g, 94.6 mmol, 13.2 mL), bis(triphenylphosphine)dichloropalladium(II) (603 mg, 0.86 mmol), and CuI (98 mg, 0.516 mmol) in DMF (26 mL) was added 4-iodo(difluoromethoxy)benzene (4.64 g, 17.2 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 20 g Celite. Flash chromatography (SiO2, Hexanes) gave 2.4 g of a dark orange oil (component A) and 1.44 g of a dark red oil (component B). Flash chromatography of Component A (SiO2, Hexanes) and Component B (SiO2, Hexanes) separately yielded 3.2 g, 72%, of the title compound as a light peach oil. MS (+ESI): m/z 345 ([M+H]+). Step 1: 1-((4-(Difluoromethoxy)phenyl)ethynyl)-3-methylbenzene To a solution of 4-iodo(difluoromethoxy)benzene (4.64 g, 17.2 mmol) in DMF (26 mL) was added TEA (9.57 g, 13.2 mL, 94.6 mmol), PdCl2(PPh3)2 (603 mg, 0.86 mmol), CuI (98 mg, 0.516 mmol), and 3-ethynyltoluene (2.5 g, 2.78 mL, 0.90 mmol). The reaction mixture was stirred for 4 h then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice more with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 20 g Celite. Flash chromatography (SiO2, Hexanes) gave 1.44 g of a dark red oil and 2.44 g of a dark orange oil. Both fractions were rechromatographed, separately, to provide 3.2 g, 72%, of the title compound as a light peach oil. 1H NMR 500 MHz (CDCl3) delta 2.33 (s, 3H); 6.50 (t, J=73.6 Hz, 1H); 7.06 (d, J=8.81 Hz, 2H); 7.12 (d, J=6.83 Hz, 1H); 7.20 (d, J=7.53 Hz, 1H); 7.30 (d, J=7.76 Hz, 1H); 7.33 (s, 1H); 7.47-7.51 (m, 2H)

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-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, A new synthetic method of this compound is introduced below., SDS of cas: 128140-82-9

A mixture of 1-(difluoromethoxy)-4-iodobenzene (1.35 g, 5.00 mmol, 1.00 equiv), 4,4,5,5- tetramethyl-2-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 ,3,2-dioxaborolane (1.413 g, 5.56 mmol, 1.10 equiv), AcOK (1.47 g, 14.98 mmol, 3.00 equiv), and Pd(dppf)C12 (186 mg, 0.25 mmol, 0.05 equiv) in dioxane (30 mL)/ water(3 mL) was stirred for 2 h at 95C under nitrogen. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:50) to afford the title compound (660 mg, 49%) as colorless oil.

The synthetic route of 128140-82-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 128140-82-9, 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. 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol A solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5 min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260. EXAMPLE 81Preparation of 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-(3hydroxyphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenolA solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5 min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260.

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-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 128140-82-9, These common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, 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.

Step 2: 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene To a mixture of 1-bromo-3-ethynylbenzene (9.1 g, 50.26 mmol), TEA (22.38 g, 30.8 mL, 221.1 mmol), PdCl2(ACN)2 (1.41 g, 2.01 mmol) and DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol). The reaction mixture became warm after the addition was completed. The mixture was stirred for 4 h. Then it was poured into water and diluted with EtOAc. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated onto 40 g Celite. Flash chromatography (SiO2, Hexanes) provided 12 g, 92%, of the title compound as a yellow oil that crystallized into a yellow solid upon standing. 1H NMR 500 MHz (CDCl3) delta6.51 (t, J=73.49 Hz, 1H); 7.08 (dd, J=1.27 Hz, 7.65 Hz, 2H); 7.19 (t, J=7.89 Hz, 1H); 7.40-7.46 (m, 2H); 7.47-7.51 (m, 1H); 7.64 (t, J=1.63 Hz, 1H) Step 2) 1-Bromo-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene To a solution of 3-bromophenylacetylene (9.1 g, 50.26 mmol), TEA (22.4 g, 221 mmol, 30.8 mL), bis(triphenylphosphine)dichloropalladium(II) (1.41 g, 2.01 mmol), and CuI (230 mg, 1.2 mmol) in DMF (60 mL) was added 4-iodo(difluoromethoxy)benzene (10.85 g, 40.21 mmol) at room temperature. The reaction mixture had gotten warm after the addition was completed. The mixture was stirred for 4 h then the mixture was portioned between EtOAc and water. The aqueous layer was separated and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated over 40 g Celite. Flash chromatography (SiO2, Hexanes) gave 12 g, 92%, of the title compound as a yellow oil that had crystallized into a solid after being undisturbed for 3d. 1H NMR 500 MHz (DMSO-d6) delta 7.34 (dt, 2H, J=8.92 Hz, 4.70 Hz); 7.42 (t, 1H, 72.99 Hz); 7.54 (t, 1H, J=7.88 Hz); 7.85-7.88 (m, 1H); 7.94-7.97 (m, 1H); 8.00 (dt, 1H, J=8.93 Hz, 4.87 Hz); 8.04 (t, 1H, J=1.80 Hz).

The synthetic route of 128140-82-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 128140-82-9,Some common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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 degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-furan-2-carboxylic acid methyl ester (119) (200mg, 0.54mmoles), 4-difluoromethoxy-1-iodo-benzene (175mg, 0.65mmoles), 2M aqueous cesium carbonate (0.81ml) and), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1 : 1) (20mg) in 1,4-dioxan (10ml), under an argon atmosphere was heated at 80C for 20h. Further quantities of 4-difluoromethoxy-1-iodo-benzene (87.5mg, 0.0.27mmoles) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1 : 1) (10mg) were added and heating at 80C was continued for 4 hours. After cooling, the mixture was concentrated. The residue was dissolved in dichloromethane and washed with water and brine, and dried. The solvent was evaporated and the residue was purified by flash chromatography using petrol (40-60)/diethyl ether 9 : 1v/v as eluent to afford compound 128 (120mg) as a wax. LC/MS System A ; Rt = 4.14 mins.

The synthetic route of 128140-82-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMAGENE LABORATORIES LIMITED; WO2004/67524; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 128140-82-9, A common heterocyclic compound, 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene, molecular formula is C7H5F2IO, 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.

[0712] Compound 655 was prepared following the similar procedure described in the synthesis of compound 593 where 1-(difluoromethoxy)-4-iodobenzene was used in place of XIII-10, and CuI Cs2CO3, and 8-hydroxyquinoline in DMSO/dioxane used as the reaction catalysts. The reaction mixture was purged with N2 and stirred at 110 C. overnight. In the last step coupling reaction, Pd-118 and K3PO4 were used in place of Pd(dppf)Cl2 and K2CO3. 1H NMR (DMSO-d6, 400 MHz) delta 8.10 (s, 1H), 7.79 (s, 1H), 7.54-7.51 (m, 3H), 7.32-7.14 (m, 4H), 6.59 (d, J=2.8 Hz, 1H), 4.51 (q, J=7.2 Hz, 2H), 3.85 (s, 3H), 1.33 (t, J=7.2 Hz, 3H).

The synthetic route of 128140-82-9 has been constantly updated, and we look forward to future research findings.