Author: Jessica.F

Electric Literature of 111771-08-5,Some common heterocyclic compound, 111771-08-5, name is 2-Fluoro-6-iodobenzoic acid, molecular formula is C7H4FIO2, 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 200 mL round- bottomed flask were added 2-fluoro-6-iodo-benzoic acid (7.5 g, 28.2 mmol), LiOH*H2O (1 .42 g, 33.8 mmol), and THF (100 mL). The resulting mixture was warmed to 50 oC and stirred for 2 h. Dimethyl sulfate (4.03 mL, 42.3 mmol) was then added and the mixture was warmed to 65 oC. After 2 h, the mixture was cooled to room temperature and NH CI(ac?) (50 mL, 13 wt% solution) was added. The two resulting layers were thoroughly mixed and then separated. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a light brown oil (7.79 g, 99% yield). 1H NMR (400 MHz, CDCIs): 7.68 – 7.60 (m, 1 H), 7.15 – 7.06 (m, 2H), 3.98 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-6-iodobenzoic acid, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
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Application of 2265-91-0,Some common heterocyclic compound, 2265-91-0, name is 1,3-Difluoro-5-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.

Compound SM (2g, 8.3mmol),CuI (100 mg, 0.5 mmol) and Pd(PPh3) 2Cl2 (350 mg, 0.5 mmol)Add to the three-necked flask, after replacing N2 three times,DMF (20 ml) and trimethylethynyl silicon (1.31 g, 13.3 mmol) were added.Replace with N2 and finally add triethylamine (1.35 g, 13.3 mmol).After the N2 substitution, the mixture was stirred at 70 C for 3 hours. After complete reaction,The system was cooled to room temperature, filtered through celite, and the filtrate was diluted with water.Extract with ethyl acetate, combine the organic phases, and wash with water.Wash once with saturated brine, dry over anhydrous sodium sulfate, filtered, and then evaporated.The oil was purified by column chromatography to give ((3,5-difluorophenyl)ethynyl)trimethylsilane (1.56 g, yield: 90%, brown oil).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,3-Difluoro-5-iodobenzene, its application will become more common.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Gang; Luo Xiaoyong; Dong Zhenwen; Li Xiaoyong; Yu Hua; Zeng Hong; Song Hongmei; Wang Ying; Wang Lichun; Wang Jingyi; (49 pag.)CN109293652; (2019); A;,
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 640280-28-0 as follows. Computed Properties of C7H3BrF3I

Intermediate C: 5-(2-Bromo-5-(trifluoromethyl)phenyl)-l-methyl-lH-pyrazole A 75-mL pressure vessel was charged with l-bromo-2-iodo-4- (trifluoromethyl)benzene (2.015 g, 5.74 mmol), l-methyl-5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-lH-pyrazole (Aldrich, St. Louis, MO, 1.374 g, 6.60 mmol), potassium phosphate (2.438 g, 11.48 mmol), and PdCi2(dppf)-CH2Ci2 adduct (Strem Chemicals Inc., Newburyport, MA, 0.469 g, 0.574 mmol). The vessel was flushed with Ar (g), then DMF (19.14 ml) was added. The vial was sealed and placed in an 80 C oil bath for 2 hours. The mixture was diluted with water and extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on an 80 g silica gel column to give 5-(2-bromo-5-(trifluoromethyl)phenyl)-l-methyl-lH-pyrazole +H]+ = 307.0.

According to the analysis of related databases, 640280-28-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Iodide – Wikipedia,
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Application of 19230-28-5, 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. 19230-28-5, name is 1,3-Dichloro-2-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 1,3-dimethyluracil 1a (0.20 mmol) in 2,2,2-trifluoroethanol (TFE) (3 mL), (4-chlorophenyl)(hydroxy)iodonium tosylate 2f (0.22 mmol) was added and it was stirred at room temperature. After completion of the reaction, the solvent was removed under vacuum. The product was then precipitated by the addition of Et2O with stirring. The precipitate was filtered to give uracil-iodonium(III) salt 3af-OTs as a white powder.

The chemical industry reduces the impact on the environment during synthesis 1,3-Dichloro-2-iodobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Takenaga, Naoko; Hayashi, Takumi; Ueda, Shohei; Satake, Hiroyuki; Yamada, Yoichi; Kodama, Tetsuya; Dohi, Toshifumi; Molecules; vol. 24; 17; (2019);,
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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C3H6I2

To a mixture of 1,3-diiodopropane (4.4 mL, 38.4 mmol) andethyl 2-oxocyclopentanecarboxylate (0.95 mL, 6.4 mmol) in acetone(16 mL) was added K2CO3 (2.3 g, 16.7 mmol), and the reactionmixture was heated under reflux for 3 days. The mixture was filtered,and the filtrate was then concentrated. The residue was purifiedby silica gel chromatography eluting with 0-50% EtOAc/hexanes to give 28 (1.44 g, 62%). 1H NMR (500 MHz, CDCl3) d4.25-4.10 (m, 2H), 3.16 (qt, J = 9.6, 6.8 Hz, 2H), 2.56-2.40 (m,2H), 2.34-2.24 (m, 1H), 2.08-1.86 (m, 5H), 1.82-1.72 (m, 1H),1.71-1.64 (m, 1H), 1.71-1.64 (m, 1H), 1.26 (t, J = 7.1 Hz, 3H).LC/MS m/z: (M+H)+ calcd for C11H18IO3, 325.03; found 325.0.

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 627-31-6.

Reference:
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
Iodide – Wikipedia,
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Application of 202865-85-8,Some common heterocyclic compound, 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, molecular formula is C7H6BrI, 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.

Under nitrogen atmosphere, 1-bromo-4-iodo-2-methylbenzene (1.0 g), (4-methoxyphenyl)methanethiol (520 mg) To a 1,4-dioxane solution (20 mL) containing tris (dibenzylideneacetone)dipalladium (80 mg) and 4,5-bis (diphenylphosphino) -9,9- dimethylxanthene (100 mg) wasadded diisopropylethylamine 1.2 mL) was added, and the mixture was reacted under reflux for90 minutes. The reaction mixture was cooled, water was added, and the mixture was extractedtwice with ethyl acetate (30 mL). The organic layer was washed with saturated brine, dried overanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtainedresidue was purified by column chromatography (heptane: ethyl acetate = 20: 1) to obtain (4 -bromo-3-methylphenyl) (4-methoxybenzyl) sulfane (907 mg, yield 83%) as a white solid.

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-iodo-2-methylbenzene, its application will become more common.

Reference:
Patent; Ishihara Sangyo Co., Ltd.; Ueki, Toshihiko; Yamada, Ryu; Izakura, Kenji; (30 pag.)JP2017/75131; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 82777-09-1, 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. 82777-09-1 name is 2′-Iodo-1,1′:3′,1”-terphenyl, 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.

(2) Synthesis of Exemplified Compound A06 [0101] [Chem.[0102] The following reagents and solvents were charged into a 100-mL recovery flask. 21 -Iodo-m-terphenyl : 925 mg (2.60 mmol) TRP-Bpin2: 453 mg (0.943 mmol) Tetrakis (triphenylphosphine) palladium ( 0 ) : 80 mg (69 mu?iotaomicron) Toluene: 20 mLEthanol: 10 mL 30-wt% cesium carbonate aqueous solution: 10 mL This reaction solution was heat-refluxed for 3.5 hours while being stirred in a nitrogen atmosphere. After the reaction was completed, the reaction solution was added with water and was stirred, and a precipitated crystal was then filtrated, followed by performing washing with water, ethanol, and acetone, so that a crude product was obtained. Next, after this crude product was heated and dissolved in toluene, this solution thus obtained was filtrated while being hot, and recrystallization was then performed using toluene as a solvent. After the crystal thus obtained was vacuum dried at 150 C, sublimation refining was performed at a pressure of 10~4 Pa and a temperature of 360C, so that 251 mg of a high-purity exemplified compound A06 was obtained (yield: 39%) . [0103] The result of identification of the obtainedcompound is shown below. [MALDI-TOF-MS] Observed value: m/z=684.35, Calculated value:[1H-NMR (400 MHz, CDC13) ]delta 8.07 (d, 2H) , 8.04 (d, 2H) , 7.99 (dd, 2H) , 7.57-7.45 (m, 6H) , 7.41 (dd, 2H) , 7.18-7.00 (m, 22H) . In addition, the Tl energy (equivalent wavelength) of the exemplified compound A06 was 469 nm measured by a method similar to that of Example 1. [0104] When the energy gap of the exemplified compound A06 was further measured by a method similar to that of Example 1, the absorption edge of the absorption spectrum was 363 nm, and the energy gap of the exemplified compound A06 was 3.42 eV. [0105] When the ionization potential of the exemplified compound A06 was further measured by a method similar to that of Example 1, the ionization potential of theexemplified compound AO 6 was 6.34 eV. [0106] Furthermore, when the LUMO level of the exemplified compound A06 was estimated by a method similar to that of Example 1, it was estimated to be -2.92 eV.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2′-Iodo-1,1′:3′,1”-terphenyl, and friends who are interested can also refer to it.

Reference:
Patent; CANON KABUSHIKI KAISHA; KOSUGE, Tetsuya; KAMATANI, Jun; KISHINO, Kengo; TOMONO, Hiroyuki; WO2011/132624; (2011); A1;,
Iodide – Wikipedia,
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Electric Literature of 98-61-3, 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. 98-61-3 name is 4-Iodobenzenesulfonyl chloride, 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.

Example 16A; N-(3-{[(4-Iodophenyl)sulfonyl]amino}phenyl)acetamide; 4-Iodobenzylsulfonyl chloride (10.0 g) is provided in isopropanol (100 ml), sodium acetate (3.12 g), which is dissolved in a little water, is added and the mixture is stirred at room temperature for 30 min. N-(3-Aminophenyl)acetamide (4.96 g) is then added and the mixture is further stirred over night. The batch is diluted with water and a saturated sodium chloride solution and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, concentrated and flash-chromatographed (eluent methylene chloride/methanol 1:0, 100:1, 80:1). 9.62 g (70% of theory) of product are obtained.HPLC (Method 6): Rt=4.14 minMS (ES+, ES-): m/z=417 [M+H]+, 415 [M-H]-,1H-NMR (400 MHz, DMSO-d6): delta=10.31 (s, 1H, NH), 9.91 (s, 1H, NH), 7.93 (d, 2H), 7.51 (d, 2H), 7.45 (s, 1H), 7.26 (d, 1H), 7.12 (t, 1H), 6.73 (d, 1H), 2.00 (s, 3H).

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

Reference:
Patent; Svenstrup, Niels; Zimmermann, Holger; Karthaus, Dagmar; Goeller, Andreas; Heimbach, Dirk; Henninger, Kerstin; Lang, Dieter; Paulsen, Daniela; Riedl, Bernd; Schohe-Loop, Rudolf; Schuhmacher, Joachim; Wunberg, Tobias; US2009/176842; (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. 19099-54-8, name is 1-Iodo-2-isopropylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 19099-54-8

General procedure: Catalyst 1 (prepared according Ref.15a, 7.1 mg,0.05 mequiv of Pd) was added to a solution of aryl iodide (4 mmol,1.0 equiv), methyl acrylate (0.72 mL, 8 mmol, 2.0 equiv), Et3N (0.67 mL,4.8 mmol, 1.2 equiv) in a mixture of toluene (6.7 mL), DMF (3.3 mL) and H2O(0.1 mL). The reaction mixture was heated at 100 C for 20 h. After coolingto rt, 1 was filtered off under vacuum. The mixture of solvents wasconcentrated under vacuum and the residue was purified by flashchromatographyon silica gel to afford pure alkenes after drying under,vacuum (0.1 mbar).

The synthetic route of 19099-54-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Derible, Antoine; Becht, Jean-Michel; Le Drian, Claude; Tetrahedron Letters; vol. 54; 32; (2013); p. 4207 – 4209;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 626-62-0, A common heterocyclic compound, 626-62-0, name is Iodocyclohexane, molecular formula is C6H11I, 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 the glove box, t-BuOLi (1 mmol, 2 equivalents, 80.1 mg) was added to the vial containing the stirrer in turn.B2pin2 (2mmol, 4 equivalents, 507.9mg), 0.85mL solvent methanol, 10muL H2O,Iodocyclohexane (0.5 mmol).The capped vial was removed from the glove box and the reaction mixture was stirred at 50 C for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a test tube by methanol, and a certain amount of internal standard n-decane was added and diluted with ethyl acetate.The yield of the product cyclohexylboronic acid pinacol ester was determined by a GC-fid method to be 30%.

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:
Patent; Peking University; Mo Fanyang; Sun Beiqi; Liu Qianyi; Hong Junting; (10 pag.)CN109575063; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com