Month: March 2021

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. 335349-57-0, name is 5-Chloro-4-iodo-2-nitroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H4ClIN2O2

Compound number 307 was prepared as follows. To a solution of [2-chloro-4-(trifluoromethyl)phenyl]boronic acid (4.5 g, 20.06 mmol) in water (30 mL) and dioxane (200 mL) was added K3PO4 (5.7 g, 26.85 mmol), 5-chloro-4-iodo-2-nitroaniline (4 g, 13.40 mmol) and Pd(PPh3)4 (800 mg, 0.69 mmol) maintained with an inert atmosphere of nitrogen and stirred overnight at 95 C. The resulting mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column with 10% ethyl acetate in petroleum ether to produce 5-chloro-4-[2-chloro-4-(trifluoromethyl)phenyl]-2-nitroaniline as a yellow solid (3 g, 32%). Next, to a solution of 5-chloro-4-[2-chloro-4-(trifluoromethyl)phenyl]-2-nitroaniline (3 g, 8.54 mmol) in ethanol (80 mL) was added hydrochloric acid (2 mL) and Zn powder (3.4 g, 52.3 mmol) in portions. The resulting solution was stirred for 2 h at reflux. The resulting mixture was concentrated under vacuum and dissolved in water (100 ml) adjusted to pH 8 with sodium carbonate and extracted with ethyl acetate (3¡Á100 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give the residue, which was purified by a silica gel column with 20% ethyl acetate in petroleum ether to produce 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenyl]benzene-1,2-diamine as brown oil (1 g, 36%). Finally, the solution of 4-chloro-5-[2-chloro-4-(trifluoromethyl)phenyl]benzene-1,2-diamine (100 mg, 0.31 mmol) in TFA (5 mL) and hydrochloric acid (conc, 1 mL) was stirred overnight at 80 C. and quenched with water (100 ml), adjusted pH to 8 with saturated aqueous sodium carbonate and extracted with ethyl acetate (3¡Á50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to give a residue, which was purified by a silica gel column with 10% ethyl acetate in petroleum ether to produce 5-chloro-6-[2-chloro-4-(trifluoromethyl)phenyl]-2-(trifluoromethyl)-1H-1,3-benzodiazole as a white solid (107.8 mg, 87%).

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; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 170112-66-0, name is 3,4,5-Trifluoroiodobenzene, 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 170112-66-0, Product Details of 170112-66-0

3, 4, 5-trifluorolactic jodoethane hydroxybenzenesulfonic (10.0g, 38.0mmol), ethyl acetate tribromoacetic difluoroaniline (23.1g, 114mmol) and dimethyl sulfoxide soln. (40 ml) of copper (2.90g, 45.6mmol) to 80 C 3 at a time. Ethyl acetate is added to the reaction mixture, by filtering the insoluble matter. The liquid water is poured, extracted with ethyl acetate. The extract is washed with saturated salt solution, and dried in an anhydrous sodium sulfate, a vacuum concentrator. Concentrated silica gel column chromatography (elution solvent: ethyl acetate/n-hexane = 1/10) by, colorless oily for compd. (yield 7.20g, yield 75%) is obtained.

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, 3,4,5-Trifluoroiodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hokko Chemical Industry Co., Ltd.; Suzuki, Jun; Kobayashi, Yuta; Morita, Motoaki; Ota, Shinya; Onoue, Shinji; Ono, Ryuta; (40 pag.)JP2016/84328; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 90347-66-3, These common heterocyclic compound, 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, 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: Iodides 2 (10.0 mmol), zinccyanide (10.0 mmol), tetrakis (triphenylphosphine) palladium (2.0 mmol) weredissolved in 20 mL DMF. The reaction was heated at 80 oC for 5 hoursunder the protection of N2. The mixture was extracted with CH2Cl2 (25¡Á3 mL) andorganic layers were combined, washed with brine, dried over Na2SO4.The solvent was evaporated under vacuum to give crude product, which waspurified by column chromatography on silica gel to give products 3-1~3-3.

The synthetic route of 90347-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Mei; Li, Shan; Ai, Jing; Sheng, Rong; Hu, Yongzhou; Hu, Youhong; Geng, Meiyu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5679 – 5684;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 628-77-3, These common heterocyclic compound, 628-77-3, name is 1,5-Diiodopentane, 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.

1 ,5-dibromopentane (0.986 g, 4.29 mmol, 0.5 eq) followed by potassium carbonate (1.30 g, 9.41 mmol, 1.1 eq) was added to a solution of 30 (3.74 g, 8.57 mmol) and tetrabutylammonium iodide (0.63 g, 1.7 mmol, 0.2 eq) in acetone (20.0 ml) in a 100 ml 20 round-bottomed flask. The reaction mixture was stirred rapidly and heated at 60 oc for 2h, and then allowed to stir at 45 oc overnight. The reaction was found complete by LCMS. The mixture was partitioned in ethyl acetate (150 ml) and water (200 ml, then washed with brine (1 00 ml), dried over magnesium sulfate. The volatiles were removed under vacuum to give the product 31 (4.04 g, 4.29 mmol, 100% Yield), which was used in the 25 next step without further purification. Analytical Data: LC/MS, 3 min lipophilic method, RT 2.39 min; MS (ES+) m/z (relative intensity) 942.3 ([M + Ht¡¤, 1 00);

Statistics shows that 1,5-Diiodopentane is playing an increasingly important role. we look forward to future research findings about 628-77-3.

Reference:
Patent; MEDIMMUNE LIMITED; DIMASI, Nazzareno; HOWARD, Philip Wilson; MASTERSON, Luke; TIBERGHIEN, Arnaud Charles; VIJAYAKRISHNAN, Balakumar; WHITE, Jason; (135 pag.)WO2019/34764; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 51628-12-7,Some common heterocyclic compound, 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, molecular formula is C8H6IN, 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 solution of the nitrile (50.0 g, 206 mmol) in toluene (500 mL) was cooled to -25 0C, then Ti(O1Pr)4 (60.3 mL, 206 mmol) was added. A commercial (Aldrich) solution of EtMgBr (3.0 M, 137 mL, 411 mmol) was then added dropwise at a rate which maintained the internal temperature between -20 and -25 0C (over approximately 60 minutes). The mixture was stirred for 60 minutes at this temperature, then the BF3OEt2 (52.1 mL, 411 mmol) was added dropwise maintaining a constant internal temperature (over approximately 30 minutes). After stirring the resulting solution for 60 minutes, the mixture was poured into 750 mL 3 N HCl(aq) and stirred rapidly for 30 minutes while warming to room temperature. The mixture was then transferred to a separatory funnel, and allowed to settle for 30 minutes. The thick yellow oil which separated on the bottom was carefully removed, then dissolved in CH2Cl2 (1 L), dried (Na2SO4) and concentrated in vacuo to provide 24 g of the amine salt (RE2a) of sufficient purity (approximately 80%) to be used directly.

The synthetic route of 51628-12-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; BERTHELETTE, Carl; BOYD, Michael; BURCH, Jason; DUFRESNE, Claude; FARAND, Julie; HAN, Yongxin; STURINO, Claudio, F.; WO2010/34110; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 116632-39-4,Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, 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.

PREPARATION EXAMPLE 36 To a mixture of 4-bromo-1-iodo-2-methylbenzene (87.5 g) and THF (400 mL) was added dropwise n-BuLi (1.55 M in hexane, 200 mL) over 50 min with dry ice-acetone bath cooling under Ar atmosphere. Then the mixture was stirred at the same temperature for 10 min. To the mixture was added a mixture of 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (56.8 g) and THF (40 mL) dropwise over 30 min at the same temperature. Then the mixture was stirred at the same temperature for 1 hour. The mixture was diluted with sat. aq. NH4Cl (200 mL) at the same temperature, and brine (100 mL) was added, and stirred at room temperature for 30 min. Then organic layer was separated, concentrated, and diluted with EtOAc (300 mL). Aqueous layer was extracted with EtOAc (300 mL), and combined organic layers were washed with brine twice, and dried over MgSO4, filtered, and concentrated under reduced pressure. To the residue was added IPE (150 mL), and the mixture was stirred at room temperature for 15 min and under ice bath cooling for 30 min. The precipitate was collected, and washed with IPE to give N-[3-(4-bromo-2-methylphenyl)oxetan-3-yl]-2-methylpropane-2-sulfinamide (48.07 g) as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-iodotoluene, its application will become more common.

Reference:
Patent; Astellas Pharma Inc.; Cytokinetics, Incorporated; SATO, Ippei; KAMIKUBO, Takashi; MIURA, Masanori; MATSUSHIMA, Yuji; TANAKA, Hiroaki; SHllNA, Yasuhiro; YAMAKI, Susumu; SAITO, Tomoyuki; KIYOHARA, Hiroshi; OHE, Munemichi; MIHARA, Kayoko; MORGAN, Bradley Paul; MALIK, Fady; COLLIBEE, Scott Emile; ASHCRAFT, Luke; LU, Pu-Ping; WARRINGTON, Jeffrey Michael; GARARD, Marc; (100 pag.)US2017/233402; (2017); 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. 766-99-4, name is 1-Ethynyl-4-iodobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Ethynyl-4-iodobenzene

General procedure: (3-Methoxypent-1-yne-1,5-diyl)dibenzene (10a) A 10 mL test tube equipped with a magnetic stirring bar was charged with IPrAu(BTZ-H) OTf (1.7 mg, 1.99 mumol, 2 mol%) and THF (200 muL, 0.5 M). To the solution were added acetal 8a (18.0 mg, 0.100 mmol) and alkyne 2a (55.0 muL, 0.500 mmol, 5.0 eq) at room temperature. The mixture was heated at 100C and the solution was stirred until TLC (hexanes-Et2O = 10 : 1) indicated a complete consumption of acetal 8a. The reaction was quenched with saturated aqueous NaHCO3 and the mixture was extracted with AcOEt three times. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (hexanes-Et2O = 60 : 1) to afford propargyl ether 10a (21.9 mg, 87.5 mumol, 87%).

The synthetic route of 766-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Furuta, Miyu; Sugiyama, Kyoko; Yamaguchi, Minami; Ueda, Hirofumi; Tokuyama, Hidetoshi; Chemical and Pharmaceutical Bulletin; vol. 67; 8; (2019); p. 872 – 876;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 61203-48-3,Some common heterocyclic compound, 61203-48-3, name is 2-Iodo-4,5-dimethoxybenzoic acid, molecular formula is C9H9IO4, 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-Iodo-4,5-dimethoxybenzoic acid (49) (2.76 g, 9.0 mmol), veratrole (1.20 g, 8.6 mmol), and 50 g of polyphosphoric acid (PPA) were heated to 90 C for 15 min. An additional 0.30 g (2.1 mmol) of veratrole was added. The reaction mixture turned a deep orange color during the reaction. The crude mixture was treated with 600 mL of ice water, sonicated, and the resultant crude product was filtered as a brownish solid (1.55 g, 40% yield). This product 50 was used without further purification

The synthetic route of 61203-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PROTEOTECH INC; ESPOSITO, Luke; YADON, Marisa, C.; CUMMINGS, Joel; HUDSON, F., Michael; LAKE, Thomas; HEFTI, Franz, F.; GOLDING, Geoffrey; CHOI, Seok-Rye; LI, Ximin; SNOW, Alan, D.; QUBAI, Hu; JUDY, Cam; WO2012/118935; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 13421-13-1, 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 13421-13-1 as follows.

General procedure: To a solution of imidazole carbaldehyde (1a-d) (100 mg, 1 equiv) in methanol (3 mL) were added successively Na2SO4 (0.2 g), amine 2a-d (1.2 equiv), alkynoic acid 3a-c (1.2 equiv) and isonitrile 4a-c (1.2 equiv) in a screw capped vial equipped with a magnetic stir bar. The reaction mixture was stirred at room temperature for 24-48 h in closed vial. After completion of the reaction, the mixture was diluted with dichloromethane (100 mL) and was extracted with water (50 mL). Organic layer was washed with brine (50 mL), dried over magnesium sulfate and evaporated under reduced pressure to obtained residue which was subjected to silica gel column chromatography (1-5 % methanol in dichloromethane) to afford the desired product 5a-r as solid.

According to the analysis of related databases, 13421-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Zhenghua; Legras, Laetitia; Kumar, Amit; Vachhani, Dipak D.; Sharma, Sunil K.; Parmar, Virinder S.; Van Der Eycken, Erik V.; Tetrahedron Letters; vol. 55; 13; (2014); p. 2070 – 2074;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, 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. Safety of Methyl 4-iodo-3-methylbenzoate

(c) Synthesis of methyl 3-methyl-4-[3-hydroxy-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propynyl]benzoate Following the basic procedure of Example 11(d), by reacting 2.4 g (10 mmol) of alpha-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol with 2.7 g (10 mmol) of methyl 3-methyl-4-iodobenzoate, 3.2 g (83%) of the expected ester, with a melting point of 130-131 C., were obtained.

The synthetic route of Methyl 4-iodo-3-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C.I.R.D. Galderma; US5716624; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com