Month: April 2021

Some common heterocyclic compound, 170112-66-0, name is 3,4,5-Trifluoroiodobenzene, molecular formula is C6H2F3I, 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. Safety of 3,4,5-Trifluoroiodobenzene

Method for preparing ethyl 2,2-difluoro-2- (3,4,5-trifluorophenyl) acetate 3,4,5-trifluoroiodobenzene (10.0 g, 38.0 mmol),Ethyl bromodifluoroacetate (23.1 g, 114 mmol)And a solution of copper (2.90 g, 45.6 mmol) in dimethylsulfoxide (40 ml)Was stirred at 80 C. for 3 hours. Ethyl acetate was added to the reaction mixture, and insoluble matter was filtered off. Pour water into the filtrate,And extracted with ethyl acetate. The extract was washed with saturated brine,After drying with anhydrous sodium sulfate,And concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (elution solvent: ethyl acetate / n-hexane = 1/10) to give the title compound as a colorless oil (yield 7.20 g, yield 75%). J = 7.3 Hz), 1.31 (3H, t, J = 7.3 Hz), 1 H NMR spectrum (CDCl 3) sigma: 7.26 (2H, t, J = 6.9 Hz), 4.31 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 170112-66-0, its application will become more common.

Reference:
Patent; Hokko Chemical Industry Co., Ltd.; Suzuki, Jun; Kobayashi, Yuta; Murakami, Hideyuki; Ono, Ryuta; Onoue, Shinji; Ota, Shinya; Nonaka, Hisato; (29 pag.)JP2016/84347; (2016); A;,
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58313-23-8, name is Ethyl-3-iodobenzoate, 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. Recommanded Product: Ethyl-3-iodobenzoate

Synthesis of 3-[2-Oxo-3-(l-phenyl-ethylidene)-2,3-dihydro-indol-l-yl]-benzoic acid ethyl ester; A Schlenk tube was charged with Cul (9.6 mg, 0.050 mmol, 5.0 mol %), 3-(l-Phenyl- ethylidene)-l,3-dihydro-indol-2-one (352.7 mg, 1.5 mmol), and K2C03 (276 mg, 2.0mmol), evacuated, and backfilled with argon. N, TV-Dimethylethylenediamine (11 uL, 0.10 mmol, 10 mol %), ethyl 3-iodobenzoate (278.8 mg, 1.01 mmol), and acetonitrile (1.5 ml) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 80 C for 23 h. HPLC monitor the reaction finished. Remove the solvent under reduced pressure. The residue was separated by flash chromatography column(gradient elution, 5-10% ethyl acetate in petroleum ether) to give 3-[2-Oxo-3-(l- phenyl-ethylidene)-2, 3 -dihydro-indol-l-yl] -benzoic acid ethyl ester as yellow powder (344 mg, 90%). 1H NMR (400 MHz, CDC13) 5ppm 1.42 (t, j=7.20 Hz, 3 H) 2.87 (s, 3 H) 4.42 (q, J=7.07 Hz, 2H) 6.25 (d, J=7.58 Hz, 1 H) 6.68 – 6.78 (m, 2 H) 7.09 (t, j=7.71 Hz, 1 H) 7.34 – 7.40 (m, 2 H) 7.47 – 7.58 (m, 3H) 7.62 – 7.72 (m, 2 H) 8.11 – 8.19 (m, 2 H) . MS calcd. for C25H2iN03 383, obsd. (ESf) [(M+H)+] 383.9.

The synthetic route of 58313-23-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; NAN, Fajun; YU, Lifang; ZHANG, Mei; CHEN, Li; HUANG, Mengwei; FENG, Lichun; LI, Jia; PANG, Tao; WO2011/32320; (2011); A1;,
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Reference of 626-62-0, 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. 626-62-0, name is Iodocyclohexane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A 2 mL crimp-top GC vial was charged with NiBr2(DME) (6.2 mg, 0.02 mmol, 0.1 equiv), dppf (11 mg, 0.02 mmol, 0.1 equiv), and activated Zn powder [35] (26.2 mg, 0.4 mmol, 2 equiv). The vial was crimped shut and the olefin (0.2 mmol, 1 equiv) was injected through the septum as a solution in 0.3 mL THF followed by 0.2 mL HFIP. The iodide (1-2 equiv) was then added (as a solution in THF, if solid) and the vial was shaken at 1000 rpm for 12 h at 25 C. The reaction was diluted with EtOAc and quenched by the addition of 1 M HCl (aq). The aqueous phase was extracted with three portionsof EtOAc. The combined organic phase was then passed through a plug of silica. An aliquot of the organic phase was used for GC or GC/MS analysis with mesitylene as an internal standard. Solvent was removed and the mixture was purified by chromatography on silicagel with EtOAc/hexane as the eluent to give the products as colorless oils.

The synthetic route of Iodocyclohexane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diccianni, Justin B.; Chin, Mason; Diao, Tianning; Tetrahedron; vol. 75; 31; (2019); p. 4180 – 4185;,
Iodide – Wikipedia,
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Reference of 791642-68-7, These common heterocyclic compound, 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, 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 4-bromo-l-iodo-2-methoxy-benzene (642 mg, 2.05 mmol) in anhydrous tetrahydrofuran (5 mL) was added n-BuLi (2.5 M, 820 uL) at -70C under a nitrogen for 30 min. Then, (¡À)-2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (360 mg, 2.05 mmol) in anhydrous tetrahydrofuran (5 mL) was added at -70C under a nitrogen for 30 min. The reaction mixture was stirred at 25C for 30 min. On completion, the reaction was quenched with saturated ammonium chloride (8 mL) and concentrated in vacuo to remove tetrahydrofuran. The residue was extracted with ethyl acetate (3 X 20 niL), dried over anhydrous sodium sulfate and concentrated in vacuo. The yellow oil was purified by silica gel chromatography (petroleum ether: ethyl acetate = 3 : 1 to 1 : 1) to give the title compound. LCMS: (ES+) m/z (M+l) + = 362.1, tR = 0.777.

The synthetic route of 791642-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (358 pag.)WO2017/156165; (2017); A1;,
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Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 626-44-8, name is 1,3,5-Triiodobenzene, 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. Recommanded Product: 626-44-8

General procedure: To a mixture of 3-methoxy-6-(trimethylsilyl)ethynylpyridazine(0.185 g, 0.766 mmol), 1,3,5-triiodobenzene (0.100 g, 0.219 mmol), Pd2(dba)3(0.020 g, 0.021 mmol), CuI (0.004 g, 0.021 mmol), PPh3 (0.005 g, 0.021 mmol) under nitrogen atmosphere were added dry Et3N (10 mL) and toluene (10 mL). The reaction mixture was cooled to 0 C and TBAF (1 M in THF, 1.53 mL) was added dropwise and the reaction mixture was stirred for 10 min. The solution was heated to50C for 48 h. The reaction was cooled,filtered through Celiteandevaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum ether/ethyl acetate2:1) to give the title compound1as a brown solid (0.055 g, 55percent). Mp: >260C. IR (cm1, neat): 1400, 2952, 2219,1582, 1538, 1466, 1423, 1403, 1335, 1296, 1166, 1133, 1098, 1010, 965,873, 841, 759, 673;1H NMR (300 MHz, CDCl3)d(ppm): 4.19 (s, 9H),7.00 (d,J9.3 Hz, 3H), 7.54 (d,J9.3 Hz, 3H) 7.84 (s, 3H);13C NMR(75 MHz, CDCl3)d(ppm): 55.3, 87.3, 89.8, 116.8, 123.3, 132.6, 135.6,143.3, 163.7; MS (TOF MS ESI);m/z(rel int. percent): (MH) 475 (100),516 (MHacetonitrile)

The synthetic route of 1,3,5-Triiodobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Martin, Flavia-Adina; Baudequin, Christine; Fiol-Petit, Catherine; Darabantu, Mircea; Ramondenc, Yvan; Ple?, Nelly; Tetrahedron; vol. 70; 15; (2014); p. 2546 – 2555;,
Iodide – Wikipedia,
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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 124700-40-9 as follows. Application In Synthesis of 2-Fluoro-4-iodobenzoic acid

2-Fluoro-4-iodobenzoic acid (61) (5.35 g, 20.1 mmol) was dissolved in methanol (30 mL, 741 mmol) was added thionyl chloride (2.6 mL, 35.8 mmol), dropwise at 0 C. with stirring. The reaction solution was then refluxed in an oil bath at 85 C. for 1 hour. Excess methanol was removed in vacuo, and benzene (20 mL) was added to the residue and then removed in vacuo. To the residue was added ethyl acetate (150 mL), and the organic layer was washed with saturated NaHCO3 (200 mL) and brine (60 mL) and then dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (150 mL SiO2, ethyl acetate:hexanes 1:48) to give compound 62 (5.3066 g, 94%) as a white crystalline solid, m.p. 76-78 C.: 1H NMR (400 MHz, CDCl3) delta 7.63 (t, J=8.0, 1H), 7.56 (dd, J=8.4, 1.6, 1H), 7.53 (dd, J=10.0, 1.2, 1H), 3.92 (s, 3H); 13C NMR (100.6 MHz, CDCl3) delta 164.4, 164.3, 162.3, 159.7, 133.5, 133.4, 133.0, 126.5, 126.3, 118.2, 118.1, 99.8, 99.7, 52.5; IR (neat) n 2952, 1700, 1595, 1561 cm-1; LC-FAB-MS (M)+ calcd for C8H6FIO2 279.9397, found 279.9394.

According to the analysis of related databases, 124700-40-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY; Wagner, Carl E.; Marshall, Pamela A.; Jurutka, Peter W.; (35 pag.)US2018/207156; (2018); A1;,
Iodide – Wikipedia,
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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. 34270-90-1, name is 1-Iodo-2-(2-iodoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Safety of 1-Iodo-2-(2-iodoethoxy)ethane

Butyllithium (2.5 M in hexanes, 3.76 mL, 9.39 mmol) was added to a solution of oxindole (500 mg, 3.76 mmol) at -78 0C in TEtaF (40 mL). After complete addition, NJSfJSf1N- tetramethylethane-l,2-diamine (1.48 mL, 9.76 mmol) was added, maintaining the internal temperature < 70 0C. After 1 h at -78 0C, 2-iodoethyl ether (4.90 g, 15.0 mmol) was added and the reaction warmed to ambient temperature. After 48 h the reaction was quenched with H2O (5 mL) and the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous solution was extracted with EtOAc (3 x 50 mL) and the combined organic layers were washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography, eluting with a gradient of CH2Cl2MeOH- 100:0 to 97:3, gave the title compound. MS: m/z = 204 (M + 1). 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 34270-90-1. Reference:
Patent; MERCK & CO., INC.; WO2006/31610; (2006); A2;,
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. 16932-44-8, name is 2-Iodo-1,3-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-1,3-dimethoxybenzene

Isopropylmagnesium chloride (10 mL, 10mmol) was added to the THF solution (60 mL) ofthe compound 1 (g [ 5.28 ], 20mmol), and it stirred at the room temperature for 1 hour. Then,the phosphorus trichloride (1.7 mL, 25mmol) was added at 78 degree C, and it stirred at theroom temperature for 2 hours. After removing a solvent and an excessive phosphorustrichloride under decompression, THF (50 mL) was added and the solution containing thecompound 2 was obtained.

According to the analysis of related databases, 16932-44-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JAPAN POLYETHYLENE CORPORATION; JAPAN POLYPROPYLENE CORPORATION; XIN, SHIXUAN; SHIMIZU, FUMIHIKO; SATO, NAOMASA; TANNA, AKIO; (45 pag.)JP5812764; (2015); B2;,
Iodide – Wikipedia,
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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. 2043-53-0, name is 1-Iodo-1H,1H,2H,2H-perfluorodecane, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Iodo-1H,1H,2H,2H-perfluorodecane

To a solution of 1H,1H,2H,2H-perfluoro-1-iododecane (8.0 g, 14 mmol) in dry ether (150 ml) at -78 C. under Ar was added t-BuLi (1.7 M in hexane; 35 ml, 21 mmol) dropwise with stirring. The mixture was stirred for 1.5 h at -78 C. and cholodiisopropylrosilane (1.7 ml, 10 mmol) was added to the reaction mixture dropwise. The mixture was stirred for 3 h and then warmed to ambient temperature. The reaction mixture was quenched with saturated NH4Cl aqueous solution and extracted with ether. The extract was dried over anhydrous MgSO4 and concentrated. The dark red liquid residue was passed through short column chromatography on silica gel with hexane to provide diisopropyl-1H,1H,2H,2H-perfluorodecanylsilane in 95% yield (5.3 g, 9.5 mmol) as a colorless liquid.

According to the analysis of related databases, 2043-53-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; University of Pittsburgh; US6897331; (2005); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 847685-01-2, A common heterocyclic compound, 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, molecular formula is C6H4F2IN, 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.

General procedure: To a two-necked round-bottomed flask fitted with a guard tube, PBr3 (2.7mmol, 0.26 mL), DMF (3 mmol, 0.23 mL) and chloroform (0.80 mL) were added, allowed to cool to 0 C and stirred for 0.5 h. After formation of colourless solid complex, 2-Iodo-4-methyl-phenylamine 2b (1 mmol) in chloroform (5 mL) was added and the reaction mixture was allowed to stir at r.t. for another 1-2 h. After completion, the reaction mixture was neutralized by adding saturated NaHCO3 solution and then extracted with DCM (3X 20 mL). Combined organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was purified through column chromatography using silica gel (60-120 mesh) and petether/EtOAc (5:1) as eluent.

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; Ghosh, Munmun; Ahmed, Atiur; Singha, Raju; Ray, Jayanta K.; Tetrahedron Letters; vol. 56; 2; (2015); p. 353 – 355;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com