Author: Jessica.F

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. 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H4F3I

General procedure: To a resealable Schlenk tube were added indole (1.0 mmol), K3PO4 (0.424 g, 2.0 mmol), and MCM-41-2N-CuI (88 mg, 0.04 mmol), and the reaction vessel was fitted with a rubber septum. The vessel was evacuated and back-filled with argon and this evacuation/back-fill procedure was repeated one additional time. The aryl halide (1.2 mmol) and toluene (2 mL) were then added under a stream of argon. The reaction tube was quickly sealed and the contents were stirred while heating in an oil bath at 110 C for 24-48 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (5 mL), and filtered. The MCM-41-2N-CuI complex was washed with distilled water (2×5 mL), ethanol (2×5 mL), and Et2O (2×5 mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (petroleum/ethyl acetate=50:1 to 4:1) to provide the desired product.

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 401-81-0.

Reference:
Article; Xiao, Ruian; Zhao, Hong; Cai, Mingzhong; Tetrahedron; vol. 69; 26; (2013); p. 5444 – 5450;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, 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. SDS of cas: 39998-81-7

Methyl-2-fluoro-4-iodo benzoate (Reagent G) A solution of 2-fluoro-4-iodo toluene (5 g, 26.6 mmol) in pyridine (2 mL) and water (20 mL) was treated with potassium permanganate (16.6 g, 105 mmol) and heated at 150 C. overnight. The reaction mixture was then cooled to room temperature and filtered and the filtrate was extracted with hexane. The aqueous phase was acidified with 10% hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was dissolved in 20 mL of methanol, treated with concentrated sulfuric acid (1 mL) and refluxed overnight. The volatiles were distilled off in vacuo and the residue was dissolved in diethyl ether, washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as an oil (0.26 g, 5%). 1H NMR (300 MHz, CDCl3):delta 7.60 (m, 4H), 3.93 (s, 3H).

The synthetic route of 39998-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan Sales, Inc.; US6252090; (2001); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25252-00-0, 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 25252-00-0 as follows.

Part C. 3′-(1-benzyl-6-cyano-1H-indol-3-ylmethyl)-4-carbamoyl-biphenyl-2-carboxylic acid benzyl ester:; 2-Bromo-5-iodobenzoic acid (6.54 g, 20.0 mmol) was dissolved in DMF (70 mL). Potassium bicarbonate (2.2 g, 22.0 mmol) was added, followed by benzyl bromide (2.8 mL, 22.0 mmol). The mixture was stirred at rt under N2 for 12 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic solution was washed with brine, dried over MgSO4, and concentrated and dried to give 9.05 g of the benzyl ester. The ester (2.3 g, 7.69 mmol), Zn(CN)2 (1.3 g, 11.5 mmol), and Pd[PPh3]4 were dissolved together in 25 mL of DMF. The mixture was de-gassed and heated at 90 C. for 4 h. Reaction mixture was concentrated and purified by chromatography (silica gel, 5% EtOAc in hexane) to give 1.8 g of the benzonitrile. MS: 316.0, 317.9 (M+1)+. The benzonitrile (1.4 g, 4.4 mmol) was dissolved in 15 mL of DMF. The reaction mixture was cooled at 0 C. Potassium carbonate (0.20 g, 1.45 mmol) was added, followed by dropwise addition of 30% hydrogen peroxide solution (1.2 mL). The cooling bath was removed and the mixture was stirred at rt for 12 h. The reaction was quenched with aqueous NaHSO3 and water. The formed precipitate was filtered and dried to give 1.1 g of the desired amide. MS: 334.2, 336.3 (M+1)+. A mixture of the resulting amide (0.2 g, 0.6 mmole), bis(pinacolato)diboron (0.228 g, 0.9 mmol) and anhydrous KOAc (0.18 g, 1.8 mmol) in 2 mL of 1,4-dioxane was purged with argon, then (1,1′)-bis(diphenylphosphino)ferrocene)palladium(II) chloride (20 mg, 0.024 mmol) was added. The resulting mixture was heated in a sealed tube in a microwave reactor at 100 C. for 2 h then left standing overnight at rt. The reaction was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the boronate (0.13 g, 57%). A mixture of this compound, the compound of Part B (0.1 g, 0.25 mmol), and K3PO4 (0.11 g, 0.5 mmol) in 5 mL dioxane was degassed and then treated with tetrakis(triphenylphosphine)palladium(20 mg, 0.017 mmol). The resulting mixture was heated in a 95-100 C. oil bath under N2 for 2 h, then stirred at rt overnight. The reaction mixture was diluted with brine and extracted 3× with EtOAc. The combined extracts were washed with brine then dried over anhydrous Na2CO3, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the product (0.12 g, 83%) as a light yellow foam. 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 2H) 4.90 (s, 2H) 5.23 (s, 2H) 6.91 (d, J=6.15 Hz, 2H) 7.05 (m, 3H) 7.20 (m, 6H) 7.29 (m, 5H) 7.42 (d, J=7.91 Hz, 1H) 7.51 (d, J=10.99 Hz, 2H) 7.98 (dd, J=8.13, 1.98 Hz, 1H) 8.19 (d, J=2.20 Hz, 1H). LC/MS m/z 576.16 (M+H)+.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); 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. 58313-23-8, name is Ethyl-3-iodobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl-3-iodobenzoate

To a solution of {l-{[(l,l-dimethylethyl)oxy]carbonyl}-5-[(phenylmethyl)oxy]-lH- indol-2-yl}boronic acid (1.13 g, 3.08 mmol), ethyl-3-iodobenzoate (0.34 mL, 2 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.126 g, 0.11 mmol), in 1,2- dimethoxyethane (35 mL) was added sodium carbonate (2 M) (4 mL, 8 mmol). The stirred reaction mixture was heated at reflux for 4 h under a nitrogen atmosphere. The reaction mixture was allowed to cool at room temperature and partitioned between water and ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give an oil. The crude product was purified by flash chromatography over silica with a hexanes: ethyl acetate gradient (100:0 to 70:30) to give an oil. The oil was dissolved in dichloromethane and the solution was concentrated to give the product. The product was dissolved in ethyl acetate and one-half of the solution was concentrated to give 0.42 g of 1,1- dimethylethyl 2- {3-[(ethyloxy)carbonyl]phenyl} -5-[(phenylmethyl)oxy]- lH-indole- 1 – carboxylate for a total yield of 0.84 g (89%). 1U NMR (400 MHz, DMSO-J6): delta 7.99 (d, J = 9 Hz, IH), 7.95 (m, 2H), 7.75 (d, J = 8 Hz, IH), 7.58 (t, J = 8 Hz, IH), 7.45 (m, 2H), 7.37 (m, 2H), 7.31 (m, IH), 7.21 (d, J = 3 Hz, IH), 7.03 (dd, J = 9, 3 Hz, IH), 6.72 (s, IH), 5.13 (s, 2H), 4.32 (q, J = 7 Hz, 2H), 1.30 (t, J = 7 Hz, 3H), 1.23 (s, 9H). ES-LCMS m/z 494 (M + Na)+.

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; SMITHKLINE BEECHAM CORPORATION; WO2009/5998; (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 181765-86-6 as follows. SDS of cas: 181765-86-6

phenanthrene-9-boronic acid (2.22 g, 10 mmol), methyl 5-bromo-2-iodobenzoate (3.41 g, 10 mmol), Pd (PPh3) 4 (0 · 21 g, 0 · 18 mmol), K2C03 solution were added to the reactor. (2 · 76g, 20mmol), deionized water 5mL, toluene 13mL, tetrahydrofuran 130mL, stirred and refluxed for 12h, after the reaction was terminated, the organic layer was separated, distilled under reduced pressure, purified by silica gel column and dried to give intermediate 7-1 ( 2.86g, 73%)

According to the analysis of related databases, 181765-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Dong Xiuqin; Cai Hui; (19 pag.)CN108774178; (2018); A;,
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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H3BrINO2

(1) Take 21.2g (100mmol) of 1-dibenzothiophene boronic acid,32.6g (100mmol) of 2-iodo-5-bromonitrobenzene,(1%) Pd (PPh3) 4,40g (300mmol) sodium carbonate,Toluene (800mL),Ethanol (200 mL) and water (200 mL),Heated to reflux, reacted for 8h, the reaction was completed;The reaction solution was extracted with ethyl acetate, and the organic phase was concentrated.A yellow solid A was obtained;

According to the analysis of related databases, 112671-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yantai Xianhua Chemical Technology Co., Ltd.; Xing Qifeng; Feng Peichuan; Chen Yue; Hu Lingfeng; Chen Yili; (28 pag.)CN110698458; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

88-67-5, name is 2-Iodobenzoic acid, 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 2-Iodobenzoic acid

General procedure: In a four-necked flask equipped with a thermometer and a stirrer, after dissolving 13.9 g of o-fluorobenzoic acid in 69.5 g of sulfuric acid and 55.6 g of DCM, 4.5 g of sodium iodate and 13.0 g of iodine were added to the reaction solution, and stirring was started to control the reaction. The temperature is 25-30 C, the reaction is kept for 1 h, and a purple solid is precipitated in the reaction liquid. After the reaction of the raw material is completed, the reaction solution is poured into a cold aqueous solution of sodium thiosulfate to be quenched, the reaction solution is spun and filtered, and 41.7 ml is used. Recrystallization of methanol gave 20 g of 2-fluoro-5-iodobenzoic acid. The yield was 75.8% and the purity was 99.0%.

The synthetic route of 88-67-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hangzhou Keyao Pharmaceutical Technology Co., Ltd.; Ren Chuan; Zhou Junming; (7 pag.)CN110078613; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 41252-96-4, name is 2-Chloro-1-iodo-4-nitrobenzene, molecular formula is C6H3ClINO2, 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. Quality Control of 2-Chloro-1-iodo-4-nitrobenzene

The 4-amino-2-chlorophenyl 2-pyridyl ketone used as a starting material was obtained as follows: n-Butyl lithium (1.6M in hexane, 12.5 ml) was added dropwise to a stirred solution of 3-chloro-4-iodonitrobenzene (5.6 g) in THF (150 ml) which had been cooled to -100 C. The mixture was stirred at -100 C. for 20 minutes. A solution of pyridine-2-carboxaldehyde (2.0 g) in THF (20 ml) was added. The mixture was allowed to warm to ambient temperature and was stirred for 16 hours. The mixture was partitioned between diethyl ether and a saturated aqueous ammonium chloride solution. The organic phase was washed with brine, dried and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained 1-(2-chloro-4-nitrophenyl)-1-(2-pyridyl)methanol (2.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41252-96-4, its application will become more common.

Reference:
Patent; Zeneca Limited; US5821246; (1998); A;,
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. 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene, A new synthetic method of this compound is introduced below., Computed Properties of C7H6BrI

Example 121, Step a-bPdCl2(Ph3P)2 (257 mg, 0.367 mmol) was added to a dioxane (45 mL) solution of l-bromo-4-iodo-2-methylbenzene (3.01 g, 10.13 mmol) and tri-«-butyl(l- ethoxyvinyl)stannane (3.826 g, 10.59 mmol) and heated at 80 0C for ~17 hours. The reaction mixture was treated with water (15 mL), cooled to ~0 0C (ice/water), and then NBS (1.839 g, 10.3 mmol) was added in batches over 7 minutes. After about 25 minutes of stirring, the volatile component was removed in vacuo, and the residue was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2, and the combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified by a gravity chromatography (silica gel; 4% ethyl acetate/hexanes)to provide bromide 121a as a brownish-yellow solid (2.699 g); the sample is impure and contains stannane-derived impurities, among others. 1H NMR (CDCl3, delta = 7.24, 400 MHz): 7.83 (s, IH), 7.63 (s, 2H), 4.30 (s, 2H), 2.46 (s, 3H).

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; BRISTOL-MYERS SQUIBB COMPANY; WO2009/102318; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 54413-93-3, 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. 54413-93-3 name is 2-Iodo-5-methoxybenzoic acid, 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-lodo-5-methoxy benzoic acid (15.0 g; 53.9 mmol) is dissolved in anhydrous DMF (45 ml) followed by the addition of 1H-1,2,3-triazole (7.452 g; 108 mmol) and cesium carbonate (35.155 g; 108 mmol). By the addition of cesium carbonate the temperature of the reaction mixture increases to 40°C and gas evolved from the reaction mixture. Copper(l)iodide (514 mg; 2.7 mmol) is added. This triggers a strongly exothermic reaction and the temperature ofthe reaction mixture reaches 70°C within a few seconds. Stirring is continued for 30 minutes. Then the DMF is evaporated under reduced pressure followed by the addition of water (170 ml) and EtOAc (90 ml). The mixture is vigorously stirred and by the addition of citric acid monohydrate the pH is adjusted to 3-4. The precipitate is filtered off and washed with water and EtOAc and discarded. The filtrate is poured into a separation funnel and the phases are separated. The water phase is extracted again with EtOAc. The combined organic layers are dried over MgSO4, filtered and the solvent is evaporated to give 7.1 g of 5-methoxy-2-(2H- 1 ,2,3-triazol-2-yl)benzoic acid as a white powder of 94percent purity (6 percent impurity is the regioisomerically Ni-linked triazolo-derivative); tR [mm] = 0.60; [M+H] = 220.21.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Iodo-5-methoxybenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BRISBARE-ROCH, Catherine; BROTSCHI, Christine; GUDE, Markus; HEIDMANN, Bibia; JENCK, Francois; SIFFERLEN, Thierry; STEINER, Michel; WILLIAMS, Jodi; WO2015/83094; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com