Category: iodides-buliding-blocks

These common heterocyclic compound, 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), 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. COA of Formula: C3H6I2

Nitrogen-extractedIn a 250 ml three-necked bottle, 2.33 g (1H-indol-2-yl)-1H-benzo[d]imidazole was weighed.(10 mmol), add 50 ml of dimethylformamide, stir well.Then add 2.8 g of potassium hydroxide (50 mmol) and stir at room temperature for 2-36 hours.As most of the potassium hydroxide dissolves, a thick, cloudy solution forms.Add 1.72 ml of 1,3-diiodopropane (15 mmol) and react at room temperature for 18-24 hours. Point board monitoring,When the reaction of raw materials is complete,The reaction was stopped and 40 ml of water and 30 ml of dichloromethane were added to the system.The mixture was further extracted with 30 ml of dichloromethane three times and the organic phases were combined and dried over anhydrous magnesium sulfate.After concentrating the organic phasePurification by column chromatography7,8-Dihydro-6H-benzo[4′,5′]imidazo[2′,1′:3,4][1,4]diaza [1,2-a]fluorene Body 1.23g, yield 45%, can be directly put into the next step reaction.

The synthetic route of 1,3-Diiodopropane(stabilized with Copper chip) has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hong Kong University Of Science And Technology Shenzhen Institute; Kuang Fuer; Li Dongsheng; Cai Peiying; (20 pag.)CN107459533; (2017); A;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 6940-76-7, name is 1-Chloro-3-iodopropane, 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 6940-76-7, COA of Formula: C3H6ClI

General procedure: In a round flask 300 mg (1.18 mmol) of compound 1 are weighed and placed in an inert atmosphere with a magnetic stirrer. Then, 3 ml of dry THF are added and the system is cooled to 0 C. Then 1.2 equivalents of LDA are added and left in an ice bath for 10 minutes. The ice bath is removed and left under constant stirring for 2 hours. The round flask is cooled again to 0 C and 1,3-chloroiodopropane is added using a syringe previously purged with nitrogen. The ice bath is removed and the reaction is followed by TLC until the consumption of the starting material (1). Once the reaction (approximately 2.5 h) is finished, 0.5 ml of a saturated NH4OH solution is added and an extraction with 5 ml of dichloromethane is carried out in triplicate, the organic phase is collected and dried with anhydrous sodium sulfate, once dried the organic phase is distilled under vacuum. The purification is carried out by a chromatographic column using silica gel as a stationary phase and a mixture of Hexane and ethyl acetate in a proportion of 95:5. A pale yellow oil is obtained in all cases.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Xavier Dominguez-Villa, Francisco; Avila-Zarraga, Gustavo; Armenta-Salinas, Concepcion; Tetrahedron Letters; vol. 61; 15; (2020);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2974-94-9, name is 1-Iodo-4-phenoxybenzene, 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 2974-94-9, Quality Control of 1-Iodo-4-phenoxybenzene

Preparation IX N-(4-phenoxyphenyl)phenylalanine A mixture of 2.17 g (7.3 mmol) of 4-phenoxyiodobenzene, 1.02 g (6.2 mmol) of phenylalanine, 0.48 g of bis(tri-o-tolylpalladium) dichloride, 125 mg of cuprous iodide, 240 mg of benzyltriethylammonium chloride and 876 mg of potassium carbonate in 12 ml of dimethylformamide, 1.2 ml of water and 2.4 ml of triethylamine is prepared. This reaction medium is stirred at 100 C. for 24 h and then cooled. 50 ml of toluene are added and the mixture is concentrated under reduced pressure. The residue is taken up with 40 ml of ethyl acetate and 40 ml of water and the mixture is acidified to pH 2. The precipitate formed is filtered off, washed with 10 ml of water and 5 ml of ethyl acetate and then dried to give 640 mg of the expected product in the form of a fine gray solid (yield=30%). M.p.=194 C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Binet, Jean; Boubia, Benaissa; Chaput, Evelyne; Edgar, Alan; Ou, Khan; Ratel, Philippe; Samreth, Soth; Thomas, Didier; US2006/25589; (2006); A1;,
Iodide – Wikipedia,
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Related Products of 624-76-0, A common heterocyclic compound, 624-76-0, name is 2-Iodoethanol, molecular formula is C2H5IO, 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.

2-Methoxy-2-methylthiopropionic acid S-(2-hydroxyethyr) ester (9); To 2.5 g (19 mmol) 8 in 20 ml of dry toluene at ice bath temperature under Ar was added 2.2 ml (14.6 mmol) DBU dropwise with stirring. Iodoethanol (1.2 ml, 14.6 mmol) in 5 ml dry toluene was added slowly to the rapidly stirred solution at O0C. The reaction mixture was then stirred for 18 hours at 5 0C. Reaction mixture was diluted with 200 ml of EtOAc and washed with 3 x 50 ml H2O. EtOAc layers were dried with Na2SO4, and solvent was removed in vacuo to give 4.7 g crude material. Silica gel chromatography with 20% EtOAc in hexanes provided 2.66 g, 79 % yield of (9). NMR 300 MHz, CDCl3, delta 3,75 (q, 2H, J=6 Hz), 3.33 (S, 3H), 3.06 (t, 2H, J=6 Hz), 2.02 (t, IH) and 1.39 (s, 6H) ppm.

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; VALEANT RESEARCH & DEVELOPMENT; WO2006/122207; (2006); 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. 33348-34-4, name is 4-Amino-3-iodobenzonitrile, A new synthetic method of this compound is introduced below., category: iodides-buliding-blocks

To a round bottomed flask equipped with an addition funnel, thermometer, reflux condenser, and nitrogen inlet were added 4-cyano-2-iodoaniline (7.88 g), acetonitrile (24 ml_), and triethylamine (4.5 ml_). Trifluoroacetic anhydride (5.0 ml.) was added to the suspension while maintaining the temperature below 35-40 0C. Note: exothermic addition is addition-rate controlled. The reaction was stirred for 30 min, diluted with water (31.5 ml_). Note: initial portion of addition is exothermic and is addition-rate controlled. The slurry was held at 15-200C for 60 min. The product was isolated by filtration. The solid was washed with 80% aqueous acetonitrile, and dried in vacuo to give the title compound as a colorless solid (9.9 g); 1H NMR (300 MHz, CDCI3) delta 8.49 (1 H, br s), 8.45 (1 H, d), 8.15 (1 H, s), 7.75 (1 H, d)

The synthetic route of 33348-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/127678; (2009); 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 101335-11-9 as follows. Formula: C6H3ClFI

Step 1. Ethyl 2-(4-(2-chloro-4-fluorophenyl)-4-hydroxycyclohexyl)acetate. A solution of n-butyllithium in hexanes (1.6 M, 81.4 mL, 130 mmol) was added dropwise to a solution of 2- chloro-4-fluoro-l-iodobenzene (16.6 mL, 130 mmol) in tetrahydrofuran (197 mL) at -78C. The reaction mixture was allowed to stir at -78C for 1 h before the addition of ethyl 2-(4- oxocyclohexyl)acetate (19.2 mL, 109 mmol) in one portion. The reaction was allowed to warm to room temperature and stirred at room temperature for 1 h. The reaction was quenched with a saturated solution of ammonium chloride (500 mL) and extracted with EtOAc (3 x 150 mL), combined organics dried (Na2S04) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica, eluting with 0-40% EtOAc in hexanes to yield the product as a colorless oil (26.7 g, 78%). 1H NMR (400 MHz, CDCb) d 7.65 (dd, / = 8.86, 6.30 Hz, 1H), 7.21 – 7.09 (m, 1H), 7.03 – 6.94 (m, 1H), 4.27 – 4.07 (m, 5H), 2.62 – 2.47 (m, 2H), 2.46 – 2.18 (m, 10H), 2.15 – 1.82 (m, 6H), 1.78 – 1.34 (m, 7H), 1.34 – 1.22 (m, 7H). [M-H2O+H] = 283.1.

According to the analysis of related databases, 101335-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DART NEUROSCIENCE, LLC; BASINGER, THOMPSON, Jillian; BOOKSER, Brett; BURLEY, Scott; GARCIA-REYNAGA, Pablo; HUDSON, Andrew; PETERS, Marco; PRATT, Benjamin; THOMPSON, Aaron; TRAN, Joe; VALDEZ, Lino; (211 pag.)WO2019/168866; (2019); 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 188815-32-9 as follows. COA of Formula: C7H4BrIO2

To a solution of 3-bromo-5-iodo-benzoic acid (commercially available from Avocado, 50g, 153 mmol, 1 equiv) in CH2CI2 (500 ml) was added 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (30.8 g, 160 mmol, 1.05 equiv), DMAP (14 g, 114 mmol, 0.75equiv) and fert-butanol (90 ml, 917 mmol, 6 equiv). The resulting mixture was stirred atroom temperature for 48 h. DMAP (4.67 g, 38 mmol, 0.25 equiv) was then added and thesolution was stirred for another 24 h then concentrated in vacua. The residue wasdissolved in AcOEt and washed sequentially with 2N aqueous HCI solution, 1N aqueousNaOH solution and brine, dried over MgSO4 and concentrated in vacua to give 1,1-dimethylethyl 3-bromo-5-iodobenzoate (D7) (50.6 g, 86%) as a brown solid which wasused in the next step without further purification.

According to the analysis of related databases, 188815-32-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/111022; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 612-55-5,Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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 an open vial with pressure-release top, a stirred mixture of 2- iodonaphthylene (Aldrich, St. Louis, MO) (64 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and ira/i5,-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred for 6 hours. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtOAc (20 mL), filtered through Celite and the filter cake washed with EtOAc (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (2 prep TLC plates used) using EtOAc / hexane (1:99) as eluent to give the product (46.2 mg, 78%) as a solid.[00215] Data identical to above in Example 5.

The synthetic route of 612-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Standard procedure: Into a flask of 150 mL of EtiO at -78 C under N2, 4-bromo-1-iodo-2-methylbenzene (22.6 g, 76.1 mmol) in anhydrous EtiO (10 mL) is added.. Then n-BuLi in hexanes (2.5 M, 26 mL, 65 mmol) is added dropwise at -78 C and stirred for an additional hour. Then, freshly prepared crude (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde (12.0 g, 21.7 mmol) dissolved in E20 (90 mL) is added via cannula over a period of 5 minutes. The mixture is stirred at -78 C for 30 min, and then slowly warmed to 0 C over a period of 1.5 h. The reaction mixture is quenched with saturated aq. NLLCl and extracted with EtOAc (250 mL x 3). The combined organic phase is washed with brine (100 mL), dried over NaiSOr and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel chromatography DCM/EtO Ac/petroleum ether to give (R)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (4.0 g, 25% yield for two steps) as a light yellow oil and (S)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (8.0 g, 51 % yield for two steps) as a light yellow oil. (R) isomer: Formula: C42H43Br06 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for 1 R: NMK (300 MHz, CDCl3) d 7.41-7.28 (m, 21H), 7.18-7.13 (m, 2H), 5.08 (d,.7= 5.1Hz, 1H), 4.71 (d, J= 11.7 Hz, 1H), 4.64-4.56 (m, 3H), 4.49 (s, 2H), 4.40 (s, 2H), 4.28 – 4.21 (m, 1H), 4.18 – 4.13 (m, 1H), 4.10 (t, J= 5.1Hz, 1H), 3.99-3.94 (m, 1H), 3.89 (t, J= 5.9 Hz, 1H), 3.83-3.70 (m, 2H), 3.49 (br. s., 1H), 2.29 (s, 3H). ESI-MS [M+Na+] calcd for (CriH-nB ENa) found: 745.5 (100%), 747.5 (97.3%) (S) isomer: Formula: C42H43BrC>6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for IS: 1H NMR (300 MHz, CDCl3) d 7.37 – 7.16 (m, 23H), 5.06 (d, J= 5.5 Hz, 1H), 4.73 – 4.67 (m, 1H), 4.62 – 4.44 (m, 7H), 4.11 – 4.03 (m, 2H), 3.85 – 3.76 (m, 3H), 3.73 – 3.67 (m, 2H), 3.19 (br. s., 1H), 2.18 (s, 3H). ESI-MS [M+Na]+ calcd for C42H43BrOeNa+ 745.21, found 745.5 (100%), 747.5 (97.3%).

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, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FIMBRION THERAPEUTICS, INC.; BISHOP, Michael Joseph; COLANDREA, Vincent J.; LI, Yuehu; STEWART, Eugene L.; STRAMBEANU, Iulia; WIDDOWSON, Katherine Louisa; JANETKA, James Walter; MCGRANE, Laurel Kathryn; (0 pag.)WO2020/12336; (2020); 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. 52548-63-7, name is 5-Fluoro-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., name: 5-Fluoro-2-iodobenzoic acid

Example 6 [00628] Preparation of Cpd 65 [00629] Step A: A mixture of 5-fluoro-2-iodobenzoic acid (9.04 g, 34.0 mmol), but-3-yn-2-ol (5.7 mL, 5.46 g, 78.0 mmol), ZnCl2 (4.62 g, 34.0 mmol), Pd(Ph3P)4 (1.96 g, 1.7 mmol), Et3N (14.2 mL, 10.3 g, 102.0 mmol) and DMF (50 mL) was stirred under argon at 100 C for 2 hours. After the removal of the volatiles under vacuum, the residue was chromatographed (silica gel, ethyl acetate in hexanes, 0-50%) to provide intermediate 7-fluoro-3-(l-hydroxyethyl)-lH- isochromen-l-one as a brown oil (5.93 g, 84%). MS m/z 209.2 [M+H]+; 1H NMR (500 MHz, CDCl3-

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; PTC THERAPEUTICS, INC.; CHEN, Guangming; DAKKA, Amal; KARP, Gary Mitchell; LI, Chunshi; NARASIMHAN, Jana; NARYSHKIN, Nikolai; WEETALL, Maria L.; WELCH, Ellen; ZHAO, Xin; WO2013/112788; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com