Category: iodides-buliding-blocks

Electric Literature of 25252-00-0,Some common heterocyclic compound, 25252-00-0, name is 2-Bromo-5-iodobenzoic acid, molecular formula is C7H4BrIO2, 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.

Oxalyl chloride (13.0 mL) is added to an ice-cold solution of 2-bromo-5-iodo-benzoic acid (49.5 g) in CH2Cl2 (200 mL). DMF (0.2 mL) is added and the solution is stirred at room temperature for 6 h. Then, the solution is concentrated under reduced pressure and the residue is dissolved in THF (100 mL). The resulting solution is cooled in an ice-bath and LiBH4 (3.4 g) is added in portions. The cooling bath is removed and the mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with THF and treated with 0.1M hydrochloric acid. Then, the organic layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried (Na2SO4) and the solvent is evaporated under reduced pressure to give the crude product. [0074] Yield: 47.0 g (99% of theory)

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

Reference:
Patent; Boehringer Ingelheim Vetmedica GmbH; ECKHARDT, Matthias; BUTZ, Tanja; HIMMELSBACH, Frank; MARTIN, Hans-Juergen; US2014/31540; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, 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 103962-05-6, Recommanded Product: 1-Iodo-4-(trifluoromethoxy)benzene

A solution of 4-bromophenol (0.173 g) in 4 mL of 1-methyl-2-pyrrolidone under argon atmosphere was treated with 4-(trifluoromethoxy)iodobenzene (0.313 mL), 2,2,6,6-tetramethylheptane-3,5-dione (0.046 mL) and caesium carbonate (0.652 g). The slurry was degassed by bubbling argon for 15 min and copper(I) chloride (0.099 g) was added. The reaction mixture was degassed by bubbling argon for 15 min, then heated to 100° C under argon for 5 h. The reaction mixture was cooled to room temperature and added dropwise to 30 mL of tert-butyl-methyl-ether. The slurry was filtered and the solids washed with tert-butyl-methyl-ether (3×20 mL). The combined filtrates were washed subsequently with 1N NaOH (50 mL), water (50 mL), 2N HCl (50 mL), 1N HCl (50 mL), water (50 mL) and brine (50 mL). The resulting organic layer was dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel eluting with hexane to afford 0.15 g of the title compound as a colourless liquid. 1H-NMR(d, ppm, CDCl3): 7.45(m, 2H); 7.20(m, 2H); 6.99(m, 2H); 6.90(m, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Iodo-4-(trifluoromethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; EP1862459; (2007); A1;,
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. 21304-38-1, name is 4-Iodobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Iodobenzene-1,2-diamine

A mixture of hexaketocyclohexane octahydrate (2.21 g, 7.08 mmol) and 4-Iodo-benzene-1,2-diamine (4.97 g, 21.24 mmol) was added to a degassed acetic acid (140 mL). The mixture was heated to 110 C for 3 hrs under nitrogen. After cooled to room temperature, the solid was collected by filtration and was washed with acetic acid to give a green solid (5.35 g, 99 % yield). ¹H (300 MHz, CD3Cl/CF3COOD) No. 9.11 (br, 3H), 8.54 (br, 3H), 8.32 (br, 3 H). HRMS EI: m/z calcd for C24H913N6 761.8023, Found 761.8087.

According to the analysis of related databases, 21304-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; WO2005/123737; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 90347-66-3

Unit Operation 1.1: 1 Sonogashira Reaction AP24595, palladium tetrakis triphenylphosphine (Pd(PPh3)4) , copper (I) iodide (Cul), triethylamine, and tetrahydrofuran (THF) are charged to the reactor. The mixture is stirred and degassed with nitrogen and then pre-degassed AP28141 is charged. The resulting mixture is brought to 45 – 55C and held for not less than 3 hours. The reaction completion is determined by IPC-1 (HPLC). If the IPC-1 criterion is met, the mixture is concentrated to a target volume and cooled. Unit Operation 1.2: Deprotection / 2nd Sonogashira Reaction AP25570, additional palladium tetrakis triphenylphosphine (Pd(PPh3)4), copper (I) iodide (Cul), and tetrahydrofuran (THF) are charged to the reactor. The mixture is concentrated and the water content is determined by IPC-2 (KF). If the IPC-2 criterion is met, the mixture is warmed to 45 – 60C and 25% sodium methoxide solution in methanol is slowly added. The reaction mixture is stirred and held for 30 – 60 minutes at 45 – 55C. The reaction progress is determined by IPC-3 (HPLC). The reaction mixture may be held at a lower temperature during the IPC analysis. If the IPC-3 criterion is met, the process is continued to Unit Operation 1.3. Unit Operation 1.3: Isolation of AP25047 HCI While stirring, the cool reaction mixture is quenched by addition of hydrogen chloride gas. A precipitate forms, and residual hydrogen chloride is removed from the suspension by a nitrogen purge. Tetrahydrofuran (THF) is replaced with toluene by an azeotropic distillation under reduced pressure. The resulting warm slurry is filtered in an agitated filter dryer and the filter cake is triturated and washed with warm toluene. The content of process impurity AP291 16 is determined by IPC-4 (HPLC). If the IPC-4 criterion is met, the wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 35 – 45C (jacket temperature). The drying is monitored by IPC-5 (LOD, gravimetric). If the IPC-5 criterion is met, the crude AP25047 HCI is discharged and packaged in FEP bags in a plastic container. The isolated AP25047 HCI can be held for up to 7 days prior to forward processing. Unit Operation 1.4: Work-up The crude AP25047 HCI solid is charged to a reactor with dichloromethane (DCM) and washed with aqueous ammonia. The aqueous phase is back extracted with DCM for yield recovery purposes and the combined organic phase is washed a second time with aqueous ammonia. The organic layer is then washed with aqueous hydrochloric acid until the aqueous phase reaches a pH of 1-2, as indicated by IPC-6 (pH strips). If the IPC-6 criterion is met, the organic phase is treated with aqueous sodium bicarbonate until the aqueous wash reaches a pH of NLT 7, as indicated by IPC-7 (pH strips). The organic phase is briefly concentrated followed by the addition of fresh dichloromethane. The organic solution is passed through a silica gel pad, which is then rinsed with additional fresh dichloromethane for increased product recovery. Unit Operation 1.5: Crystallization of AP25047 The dichloromethane solution is concentrated under reduced pressure, and the dichloromethane is replaced with 2-propanol by azeotropic distillation under reduced pressure to the targeted final volume range. The resulting suspension is then cooled and further aged with agitation. Unit Operation 1.6: Isolation / Drying The precipitated product is isolated in an agitated filter dryer under a flow of nitrogen, and the filter cake is rinsed with 2-propanol. The wet filter cake is dried with agitation under a flow of nitrogen and reduced pressure at 45 – 55C (jacket temperature). The drying is monitored by IPC-8 (LOD, gravimetric). If the IPC-8 criterion is met, the product is sampled and packaged into polyethylene bags and placed within a heat sealed mylar coated aluminum foil bag, within an HDPE shipping container (Expected yield range, 65 – 89%).

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

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; MURRAY, Christopher, K.; ROZAMUS, Leonard, W.; CHABER, John, J.; SHARMA, Pradeep; WO2014/93579; (2014); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103962-05-6,Some common heterocyclic compound, 103962-05-6, name is 1-Iodo-4-(trifluoromethoxy)benzene, molecular formula is C7H4F3IO, 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 of intermediate H A solution of intermediate G (100 mg, 0.504 mmol), l-iodo-4-(trifluoromethoxy) benzene (CAS [103962-05-6], 145 mg, 0.504 mmol), X-Phos (28.8 mg, 0.06 mmol), Pd(dba)2 (17.4 mg, 0.03 mmol) and t-BuONa (194 mg, 2.02 mmol) in dioxane (4 mL) was irradiated under microwave at 100°C for 1 hour under N2. The mixture was concentrated. The crude product was purified by column chromatography over silica gel (eluent: ethyl acetate / petroleum ether from 0 to 1/1). The desired fractions were collected and concentrated to give intermediate H (100 mg, yield: 55percent).

The synthetic route of 103962-05-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; GUILLEMONT, Jerome, Emile, Georges; MOTTE, Magali, Madeleine, Simone; RABOISSON, Pierre, Jean-Marie, Bernard; TAHRI, Abdellah; (194 pag.)WO2017/1660; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 640280-28-0, The chemical industry reduces the impact on the environment during synthesis 640280-28-0, name is 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, I believe this compound will play a more active role in future production and life.

Example 36: 5-(2-(l,2,3,6-Tetrahydropyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2- yl)-3 ,4-dihydroisoquinoline-2( 1 H)-sulfonamide hydrochloride Step 1 : tert-Butyl 4-(2-(isoquinolin-5-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine- 1 (2H)-carboxylate A solution of Ci2Pd(dppf)-CH2Ci2 adduct (Strem Chemicals Inc., Newburyport, MA, 1.157 g, 1.416 mmol), (n-tert-butoxycarbonyl)-l,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester (8.76 ml, 28.3 mmol), l-bromo-2-iodo-4-(trifluoromethyl)benzene (9.94 g, 28.3 mmol), and potassium phosphate (36.1 g, 170 mmol) in 100 mL dioxane, 40 mL water was heated to 100 C 3 hours. LC/MS showed complete consumption of starting material. Isoquinolin-5 -ylboronic acid (4.90 g, 28.3 mmol) and Ci2Pd(AmPhos) (Sigma-Aldrich, St. Louis, MO, 1.003 g, 1.416 mmol) were added, and the reaction mixture was again heated to 100 C for an additional hour. The reaction mixture was allowed to cool to room temperature and was diluted with diethyl ether. The organics were washed with water, then brine, dried over MgS04 and concentrated. Purification of the resulting residue by si81ica gel column chromatography (0 to 100% EtO Ac/heptane) gave tert-butyl 4-(2-(isoquinolin-5-yl)-5- (trifluoromethyl)phenyl)-5,6-dihydropyridine-l(2H)-carboxylate (9.80 g, 21.56 mmol).

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, 1-Bromo-2-iodo-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 2043-55-2, The chemical industry reduces the impact on the environment during synthesis 2043-55-2, name is 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane, I believe this compound will play a more active role in future production and life.

Example 2 Synthesis of 1-iodo-5,5,6,6,7,7,8,8,8-nonafluorooctane Anhydrous tetrahydrofuran (200 ml) was added to 60percent sodium hydride (2.78 g, 69.52 mmol) and the resulting mixture was cooled to 0° C. Diethyl malonate (12.18 ml, 80.22 mmol) was slowly added dropwise to this mixture, which was then stirred for 1 hour at room temperature. A solution of 1-iodo-3,3,4,4,5,5,6,6,6-nonafluorohexane (20.0 g, 53.48 mmol) in anhydrous tetrahydrofuran (50 ml) was then slowly added dropwise to the mixture, followed by stirring for 12 hours at room temperature. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/50) to give diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (19.4 g, Yield 89percent). 1H-NMR(300 MHz, CDCl3): delta 4.24(q, 4H), 3.41(t, 1H), 2.30-2.19(m, 4H), 1.28(t, 6H).

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, 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; US6552069; (2003); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 25309-64-2,Some common heterocyclic compound, 25309-64-2, name is 1-Ethyl-4-iodobenzene, molecular formula is C8H9I, 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 2 (120mg, 0.37mmol) was dissolved in DMF (0.8mL, 0.47mol / L), was added Et3N (0.14mL, 1.11mmol), 1- ethyl-4-iodo-benzene (97.2mg, 0.42mmol), stir, add Pd (OAc)2(3.71mg, 0.017mmol), gradually warmed to 80 , heated to reflux for 8h, the reaction was monitored by TLC, After completion of the reaction, the reaction solution was cooled to room temperature.Addition of distilled water (20mL), and extracted with anhydrous diethyl ether (20mL × 5), and the organic layer was washed with Na2SO4Drying, rotary evaporation, purified by silica gel column to give product 3E (78% yield) and 4E (yield 12%).

The synthetic route of 25309-64-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Shang De Yaoyuan Technology Co., Ltd.; Nankai University; Chen Yue; Zhang Quan; Fan Hongxia; Ding Yahui; Long Jing; (16 pag.)CN104211669; (2018); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 19099-54-8, 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. 19099-54-8, name is 1-Iodo-2-isopropylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

0.3 mmol of sodium carbonate and 0.1 mmol of 1,2-bis(4-methoxyphenyl)acetylene,Tetrakis(triphenylphosphine palladium) 0.005 mmol, bis(2-diphenylphosphinophenyl)ether 0.005 mmol,0.2 mmol of (4-(benzyloxy)phenyl)boronic acid, 0.3 mmol of 2-isopropyliodobenzene, and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube.Nitrogen was repeatedly filled 10 times, placed in an oil bath at 120 C, and reacted for 24 hours;Cooled to room temperature, the reaction was diluted with ethyl acetate, washed with water three times, the organic phase dried over anhydrous Na2SO4, filtered, and concentratedPurification by thin layer chromatography to give 31.8mg of the desired product, yield 53%.

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, 1-Iodo-2-isopropylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Huaqiao University; Cheng Guolin; Lv Weiwei; (20 pag.)CN109879713; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 69113-59-3, These common heterocyclic compound, 69113-59-3, name is 3-Iodobenzonitrile, 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: Aryl iodide 3 (0.2 mmol, 1.0 equiv), acrylate/styrene 4 (0.202 mmol, 1.01 equiv), DIPEA (28.4 mg, 0.22 mmol, 1.1 equiv), and Pd(I)-iodo dimer 2 (1.3 mg, 0.0015 mmol, 0.75 mol%) were weighed into a 4 mL screw cap vial, purged with argon, and dissolved in anhydrous toluene(1.5 mL). The vial was capped with a PTFE-lined screw cap and sealed with PTFE tape prior to heating to 100 C under stirring by using an aluminum heating block outside the glovebox. After 15 h, the reaction mixture was allowed to cool to r.t. and diluted with EtOAc (to 20 mL); excess base was quenched by the addition of sat. aq NH4Cl (20 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (2*20 mL). The combined organic layer was dried over MgSO4 and the solvent was removed under reduced pressure. The obtained crude product was purified by flash column chromatography.

Statistics shows that 3-Iodobenzonitrile is playing an increasingly important role. we look forward to future research findings about 69113-59-3.

Reference:
Article; Sperger, Theresa; Stirner, Christopher K.; Schoenebeck, Franziska; Synthesis; vol. 49; 1; (2017); p. 115 – 120;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com