Category: 64248-58-4

Application of 64248-58-4, A common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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 solution of compound 33b, 4-Methyl-2-(5-piperidin-3-yl-4′-trifluoromethyl-biphenyl-3-yl)-pentanoic acid ethyl ester (110 mg, 0.25 mmol) in dimethylsulfoxide (0.2 ml) was added L-proline (4.4 mg, 0.04 mmol), potassium carbonate (52.5 mg, 0.38 mmol), and copper iodine (3.6 mg, 0.02 mmol). The reaction was degassed under nitrogen and 1,2-difluoro-4-iodobenzene (45.4 mg, 0.19 mmol), was added, the reaction was again degassed and then heated to 90 C. The reaction was stirred over 48 hours. The reaction was partitioned between EtOAc/H2O, washed with H2O (3×) and brine (1×). Purification by silica gel chromatography (Isco) gave the desired product, (39 mg, 37%). Calcd for C32H34F5NO2 (M+H) 559.60, Found 560.4.

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HO, Chih Yung; US2009/105275; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 64248-58-4,Some common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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 zinc dust (980 mg, 15 mmol, Aldrich, -325 mesh) and dry tetrahydrofuran (3 mL) under argon was treated with 1,2-dibromoethane (0.37 g, 2 mmol). The zinc suspension was then heated with a heat gun to ebullition, allowed to cool, and heated again. This process was repeated three times to make sure the zinc dust was activated. The activated zinc dust suspension was then treated with trimethylsilyl chloride (82 mg, 0.75 mmol), and the suspension was stirred for 15 min at 25 C. The reaction mixture was then treated dropwise with a solution of (E)-3-cyclohexyl-2-iodo-acrylic acid methyl ester (prepared in Example 4, 1.47 g, 5 mmol) in dry tetrahydrofuran (1.5 mL) over 3 min. During the addition, the temperature rose to 45 C. The reaction mixture was then stirred at 40-45 C. for 1 h and then stirred overnight at 25 C. The reaction mixture was then diluted with dry tetrahydrofuran (5 mL), and the stirring was stopped to allow the excess zinc dust to settle down (2 h). In a separate reaction flask, bis(dibenzylideneacetone)palladium(0) (54 mg, 0.1 mmol) and triphenylphosphine (104 mg, 0.4 mmol) in dry tetrahydrofuran (10 mL) was stirred at 25 C. under argon for 10 min and then treated with 3,4-difluoro-iodobenzene (960 mg, 4 mmol) and the freshly prepared zinc compound in tetrahydrofuran. The resulting brick red solution was heated at 25 C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution (50 mL), and the organic compound was extracted into diethyl ether (250 mL), The combined organic extracts were washed with a saturated aqueous sodium chloride solution (150 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 5/1 hexanes/diethyl ether) afforded (E)-3-cyclohexyl 2-(3,4-difluoro-phenyl)-acrylic acid methyl ester (1.06 g, 95%) as an oil: EI-HRMS m/e calcd for C16H18F2O2 (M+) 280.1275, found 280.1275.

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

Reference:
Patent; Hoffmann-La Roche Inc.; US6353111; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 64248-58-4, 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. 64248-58-4 name is 1,2-Difluoro-4-iodobenzene, 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.

To a degassed (argon) solution of 1,3-dihydro-2H-imidazol-2-one (1.75 g, 18.75 mmol) and 3,4-difluoroiodobenzene (3 g, 12.5 mmol) in dimethylsulfoxide (20 mL) was added, palladium(II) acetate (0.14 g, 0.62 mmol) and sodium acetate trihydrate (3.07 g, 37.5 mmol) at ambient temperature. The reaction mixture was further degassed with argon and stirred at 80 C for 16 h. The reaction mixture was cooled to ambient temperature, filtered through Celite diatomeaceaus earth filter aid and washed with ethyl acetate (2 × 50 mL). The filtrate was then washed with water (2 × 25 mL) and the crude product was purified by silica gel chromatography. Elution with 5% methanol in dichloromethane provided the title compound as a white solid (670 mg). 1H NMR (400MHz) delta 6.97 (s, 1H), 7.34-7.44 (m, 2H), 7.55-7.61 (m, 1H), 10.12 (s, 1H), 10.54 (s, 1H). MS (M+1) = 195.2

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Difluoro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; SATTERFIELD, Andrew Duncan; (105 pag.)WO2017/23515; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 64248-58-4, These common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-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.

In a 50- mL RB-flask was added [3- (4-HYDROXYPHENYL)] propionic acid (1.66 g, [10.] 0 mmol), 3,4-difluoroiodobenzene (2.40 g, 10.0 mmol), copper (I) bromide (0.100 g), potassium carbonate (2.76 g, 20.0 [MMOL),] and [N-METHYL-2-PYRROLIDONE] (20 [ML)] as solvent. The mixture was stirred for 5 min at room temperature and then heated to [140 C] (oil bath). After being stirred for 12 hours at [140 C,] the reaction mixture was cooled to room temperature and diluted with [ETOAC] (100 mL). The diluted mixture was washed with citric acid (aq, 30 mL), water (3 x 50 mL, brine and dried over [MGS04. THE] removal of solvent in vacuo afforded crude which was purified by chromatography (0.901 g, [32%)] : [1H] NMR (400 MHz, CDCl3) 8 11.44-11. 06 (br, 1H), 7.24-7. 14 (m, 2H), 7.14-7. 00 (m, [1H),] 7.00-6. 86 (m, 2H), 6.86-6. 75 (m, 1H), 6.75-6. 61 (m, 1H), 2.94 (t, 2H, J = 7.6 Hz), 2.68 (t, 2H, [J = 7.] 6 Hz); ESMS [M/E] : 277.2 (M-H+).

Statistics shows that 1,2-Difluoro-4-iodobenzene is playing an increasingly important role. we look forward to future research findings about 64248-58-4.

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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Difluoro-4-iodobenzene

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl2 (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na2CO3 (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N2 and stirred at 110 C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH3OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4, concentrated and purified on silica using EtOAc/Heptane 1:20 ? 1:9 step gradient) to afford 2′-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

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:
Article; Saleeb, Michael; Mojica, Sergio; Eriksson, Anna U.; Andersson, C. David; Gylfe, Asa; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1077 – 1089;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, name is 1,2-Difluoro-4-iodobenzene, belongs to iodides-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. Quality Control of 1,2-Difluoro-4-iodobenzene

A mixture of methyl indole-5-carboxylate 24a (2 g, 11.4 mmol), 1-iodo-3,4-difluoro-benzene 24b (1.5 mL, 12.5 mmol), CuI (0.22 g, 1.14 mmol), trans-N,N’-dimethylcyclohexane-1,2-diamine (0.54 mL, 3.43 mmol), and K3PO4 (6.06 g, 28.5 mmol) in toluene (12 mL) was heated at 110 C. for 7 hours. The reaction mixture was diluted with CH2Cl2 and filtered. The solution was concentrated and the residue was purified by flash column chromatography (silica gel, 20% EtOAc/heptane) to give 24c (3.0 g).

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Connolly, Peter J.; Macielag, Mark J.; McDonnell, Mark E.; Zhu, Bin; US2012/77797; (2012); 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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H3F2I

Add bis (triphenylphosphine) palladium (II) dichloride (49 mg, 0. 07 mmol), copper (I) iodide (28 mg, 0. 15 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (200 mg, 1. 5 mmol) to a solution of 1, 2-difluoro-4-iodobenzene (420 mg, 1. 7 mmol) in triethylarnine (3. 1 mL, 22 mmol) and heat at 60 C for 16 h. Cool to room temperature and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient of 50 : 50 to 100 : 0 dichloromethane : hexanes, followed by a second silica gel chromatography, eluting with 95 : 5 to 85 : 15 hexanes : ethyl acetate to give the title compound as a white solid (320 mg, 88%). 1H NMR (300 MHz, Cd13) 8 7. 14-7. 23 (m, 1H), 7. 28-7. 40 (m, 2H), 7. 76-7. 82 (t, J = 2. 0 Hz, 1H), 8. 51-8. 55 (d, J = 2. 3 Hz, 1H), 8. 59-8. 62 (d, J = 1. 8 Hz, 1H), MS (APCI) : m/z= 250 [M+H] +.

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 64248-58-4.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 64248-58-4 as follows. Application In Synthesis of 1,2-Difluoro-4-iodobenzene

a) (3,4-Difluoro-phenyl)-propynoic acid ethyl ester (Vc) Under argon atmosphere, a four neck flask was charged with THF (135 ml) and 2 M LDA in THF (60.9 ml, 0.12 mol, 1.18 eq.) and cooled to -78 C. Propynoic acid ethyl ester (12.2 g, 0.12 mol, 1.18 eq.) dissolved in THF (36 ml) was added dropwise within 30 min. Then, ZnBr2 (28.5 g, 0.12 mol, 1.2 eq.) dissolved in THF (45 ml) was added dropwise within 30 min. After the addition of 1,2-Difluoro-4-iodo-benzene (25.0 g, 0.10 mol) and tetrakis(triphenylphosphine) palladium(0) (6.02 g, 5.15 mmol, 5 mol %), the reaction mixture was allowed to warm to r.t. and stirred for another 3 h at the same temperature. The reaction mixture was diluted with diethylether and washed with saturated aqueous NH4I, saturated aqueous NaHCO3 and brine. The organic phase was dried with Na2SO4, concentrated under reduced pressure and dried under vacuum. The residue was purified by silica gel filtration (heptane/ethyl acetate 98:2) to yield 16.6 g (76%) of Vc as light yellow oil. ES-MS m/c: 210 (M+).

According to the analysis of related databases, 64248-58-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-Emery, Fabienne; Puentener, Kurt; Ratni, Hasane; US2010/152462; (2010); 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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Difluoro-4-iodobenzene

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl2 (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na2CO3 (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N2 and stirred at 110 C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH3OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4, concentrated and purified on silica using EtOAc/Heptane 1:20 ? 1:9 step gradient) to afford 2′-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

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:
Article; Saleeb, Michael; Mojica, Sergio; Eriksson, Anna U.; Andersson, C. David; Gylfe, Asa; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1077 – 1089;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 64248-58-4,Some common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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.

General procedure: PPh3 (1.3 mmol, 1.3 equiv), I2(1.3 mmol, 1.3 equiv) and4 cm3 toluene were added to a 20 cm3 test tube equipped witha stir bar, which was stirred for 10 min at room temperature.Then, aryl iodide 1, 4, or 5 (1 mmol), alkyne 2 (1.5 mmol,1.5 equiv), Pd(OAc)2 (3 mol%), and Et3N(5 mmol, 5 equiv)were added into the solution. At last, HCOOH (2 mmol, 2equiv) was added, and the tube was immediately sealed andstirred at 40 C for 4 h. After completion of the reaction,mixture was cooled to room temperature, filtered, and concentratedunder reduced pressure. The obtained residue waspurified by flash column chromatography on silica gel toprovide the corresponding products 3, 6, or 7.

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

Reference:
Article; Lyu, Xue; Sun, Guanglong; Zhou, Yang; Wang, Yingying; Lei, Min; Wu, Wanying; Guo, Dean; Monatshefte fur Chemie; vol. 150; 2; (2019); p. 309 – 315;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com