Category: iodides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 161949-50-4, name is 2-Chloro-5-iodoanisole, 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 161949-50-4, name: 2-Chloro-5-iodoanisole

2nd reaction step: 4-Chloro-3-methoxybenzeneboronic acid In a flame-dried flask, 1.93 g (79.2 mmol) of magnesium turnings were etched with a small crystal of iodine, and 50 ml of anhydrous ether were added. Then, under a nitrogen atmosphere, a solution of 20.0 g (79.2 mmol) 2-chloro-5-iodoanisole in 50 ml of anhydrous ether were added dropwise in such a way that the ether was kept boiling by the heat of reaction. After the addition was complete, the mixture was refluxed for 11/2 hours and then filtered through glass wool, with exclusion of moisture, into a dropping funnel. This Grignard solution and, synchronously but separately, 8.24 g (79.2 mmol) of trimethyl borate were added dropwise to 50 ml of anhydrous ether in a flame-dried flask under a nitrogen atmosphere at -60 to -70 C. The resulting suspension was then stirred at the stated temperature for one hour and, after it had warmed to about 20 C., acidified to pH 3 with 5% strength sulfuric acid. After separation of the phases, the aqueous phase was extracted three times with ether. The combined organic phases were dried over sodium sulfate and then concentrated. The residue was extracted by boiling three times with 100 ml of water each time. The aqueous phases were combined and cooled, when 4.6 g (32%) of colorless crystals separated out and were removed and dried under reduced pressure at 20-25 C. 1 H-NMR (270 MHz, in d6 -DMSO): delta [ppm]=3.90(s,3H), 7.39(s,2H), 7.56(s,1H), 8.2(s,br.,2H).

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, 2-Chloro-5-iodoanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BASF Aktiengesellschaft; US5783522; (1998); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 4028-63-1, A common heterocyclic compound, 4028-63-1, name is 2,4,6-Trimethyliodobenzene, molecular formula is C9H11I, 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: A 10 mL flask equipped with a Teflon valve was charged with a magnetic stir bar, CuI (2 mg, 1molpercent), Heteroarylamine (1.5 mmol), KOtBu (224 mg, 2.0 mmol), solid aryl halides (1.0 mmol). The tube was evacuated and backfilled with argon. Under a counter flow of argon, dioxane (1.5mL), aryl halides (1.0 mmol, if liquid) were added by syringe. The tube was sealed. The reaction mixture was allowed to stir at 110 ¡ãC (X=I) or 130 ¡ãC (X= Br) for 24 h. Then the mixture was cooled to room temperature and added 5.0 mL brine. Subsequently, the mixture was extracted with ethyl acetate. The organic layers were collected, dried over Na2SO4, filtered and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel.

The synthetic route of 4028-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Deping; Kuang, Daizhi; Zhang, Fuxing; Liu, Yang; Ning, Shunhua; Tetrahedron Letters; vol. 55; 51; (2014); p. 7121 – 7123;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 61272-76-2, 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. 61272-76-2, name is 4-Fluoro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-Iodoaniline 2a (65.7 mg, 0.3 mmol), Cu(OAc)2 (6 mg, 10percent), KOtBu (101 mg, 0.9 mmol), DMAc (1.0 mL) were mixed in a Schlenck tube and then to the mixture was added 2-(phenylethynyl)benzonitrile1a (74 mg, 0.36 mmol) under N2. The reaction mixture was stirred for 12 h at 120 ¡ãC under N2. After the reaction was completed (monitored by TLC), the reaction mixture was then diluted with water and extracted with ethyl acetate. After the combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure, the residue was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate as eluent to afford the pure product 3

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 77317-55-6,Some common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, molecular formula is C8H8INO2, 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.

Example 2: Synthesis of methyl 5-iodo-2-(nitro amino) benzoatewherein X is I and R is Me. One hundred g of methyl 2-amino-5-iodobenzoate was dissolved in 1000 ml of acetic acid. Then 100 ml of fuming nitric acid was added to the reaction solution at 150C slowly so that the internal temperature did not exceed 2O0C. The reaction solution was stirred for 30 minutes. Afterwards, 110 ml of acetic anhydride was added to the reaction solution at 2O0C or less, followed by stirring for 1 hour. Then the reaction solution was poured into 2 L of ice water, stirred for 30 minutes, and filtered to obtain 104 g (yield: 90%) of the compound of interest which is in a yellowish solid: 1H NMR (300 MHz, DMSO), delta 8.19 (d, IH, J=2Lambda Hz), 8.07 (dd, IH ,J=8.7, 2.1 Hz), 7.21 (d, IH, J=8.7 Hz), 3.80 (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 Methyl 2-amino-5-iodobenzoate, its application will become more common.

Reference:
Patent; PHARMACOSTECH CO., LTD.; KIM, Jae Won; CHA, Young Gwan; RYU, Hyung Chul; KIM, Sun Joo; KIM, Sang Hyun; JEON, Tae Hong; WO2010/67912; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 51560-21-5,Some common heterocyclic compound, 51560-21-5, name is 1,4-Diiodo-2,5-dimethoxybenzene, molecular formula is C8H8I2O2, 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: according to the Mizoroki-Heck reaction (Scheme 1). First; by thecoupling between 4-substituted styrenes and dibromo or diiodobenzenes(Method A, Scheme 1), and second; the reaction between4-substituted bromo or iodobenzenes with 1,4-divinylbenzene(Method B, Scheme 1).The general procedure is as follows: 2.05 equivalents of thecorresponding styrene and 1 equivalent of 1,4-dibromo or 1,4-diiodobenzene (Method A, to OPVs 1a-d and 2a-f) or 2.05 equivalentsof the appropriate aryl halide and 1 equivalent of 1,4-divinylbenzene (Method B, to OPVs 1e-h), were placed in a 10 mLheadspace crimp vial equipped with a magnetic stir bar. Then, forboth methods, it was added 0.01 equivalents (1 mol%) of Pd(dba)2,0.1 equivalents (10 mol%) of P(OPh)3 and 5 equivalents of TEA. Thevial was sealed with a PTFE/silicone septum with aluminum capand purged-saturated with N2, then 2 mL of solvent was injected(dry DMF for OPVs-series 1 and 1,4-dioxane for OPVs-series 2,Scheme 1) and the system was purged once again with N2. Thereaction mixture was vigorously stirred at 110 C during 48 h forOPVs-series 1 and 24 h for OPVs-series 2. After finished, highlyfluorescent solid products were obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Diiodo-2,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Estrada, Sandra E.; Ochoa-Puentes, Cristian; Sierra, Cesar A.; Journal of Molecular Structure; vol. 1133; (2017); p. 448 – 457;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

202982-67-0, name is 4-Chloro-3-fluoroiodobenzene, 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. Computed Properties of C6H3ClFI

To a solution of 1-chloro-2-fluoro-4-iodobenzene (5.72 g, 22.67 mmol) in 1, 4-dioxane (150 mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (6.00 g, 22.67 mmol), Pd (dppf) Cl2 (2.47 g, 3.38 mmol) and Cs2CO3 (11.00 g, 33.83mmol) and the mixture was heated at 80 for overnight. Then evaporated the solvent under reduced pressure and the residue was purified by column chromatography (PE: EA = 20: 1) to give product as a clear oil (4.06 g in 67% yield). 1H NMR (DMSO-d6) deltaH 7.51 (t, J= 8.0 Hz, 1H), 7.46 (m, 1H), 7.28 (m, 1H), 7.12-7.20 (m, 1H), 3.91 (s, 4H), 2.51-2.56 (m, 2H), 2.34-2.40 (m, 2H), and 1.80 (t, J = 6.8 Hz, 2H).

The synthetic route of 202982-67-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); 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 31599-61-8 as follows. COA of Formula: C8H9I

General procedure: In the flame-dried Schlenk flask (50 mL), equipped with magnetic stirrer and inert gas inlet secondary phosphine oxide 18 (0.546 g, 0.003 mol) was dissolved in toluene (5 mL). Then, aryl iodide (3,4-dimethyliodobenzene (0.696 g, 0.426 mL, 0.003 mol) or 4-iodotoluene (0.655 g, 0.003 mol)) was added, followed by CuI (0.057 g, 0.300 mmol), alpha-phenylethylamine (0.073 g, 0.077 mL, 0.600 mmol) and K2CO3 (0.829 g, 0.006 mmol). The mixture was heated at reflux for 24 h, then cooled to room temperature. Saturated NH4Cl solution (15 mL) was then added and the mixture was extracted with CHCl3 (3¡Á40 mL). The organic phase was dried over MgSO4 and evaporated and the residue was purified by flash chromatography using CHCl3:MeOH 50:1 as eluent yielding 15b (0.808 g, 94%) as white solid or 15e (0.727 g, 89%) as pale yellow solid.

According to the analysis of related databases, 31599-61-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stankevi?, Marek; Pisklak, Jolanta; W?odarczyk, Katarzyna; Tetrahedron; vol. 72; 6; (2016); p. 810 – 824;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 13194-67-7, These common heterocyclic compound, 13194-67-7, name is 4-Fluoro-2-iodo-1-methylbenzene, 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.

N-Bromosuccinimide (NBS, 3.77 g, 21.2 mmol) and benzoyl peroxide (77 mg,0.32 mmol) were added to a solution of 4-fluoro-2-iodo-1-methylbenzene 10d (5 g, 21.2 mmol) inCCl4 (55 mL). The mixture was heated to reflux for 60 hours then cooled to room temperature. The mixture was concentrated under reduced pressure. Purification over silica eluting with pentane provided the title compound as a white solid (3.67 g, 52% yield). 1H NMR (400MHz, CDCl3):d 7.57 (dd, 1H), 7.45 (dd, 1H), 7.06 (m, 1H), 4.58 (s,2H); Also a known commercially available compound.

Statistics shows that 4-Fluoro-2-iodo-1-methylbenzene is playing an increasingly important role. we look forward to future research findings about 13194-67-7.

Reference:
Article; Roberts, Lee R.; Corbett, Matthew S.; Fussell, Steven J.; Hitzel, Laure; Jessiman, Alan S.; Mason, Helen J.; Osborne, Rachel; Ralph, Michael J.; Stennett, Adam S.D.; Wheeler, Simon; Storer, R. Ian; Tetrahedron Letters; vol. 56; 47; (2015); p. 6546 – 6550;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

148870-57-9, name is 7,8-Dimethoxy-3-(3-iodopropyl)-1,3-dihydro-2H-3-benzazepin-2-one, 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. Recommanded Product: 148870-57-9

Based on EP 0 534 859 [0053] A solution of the (d) camphorsulphonate salt obtained in Example 4 in ethyl acetate is brought to basic pH using sodium hydroxide and then the organic phase is separated off, washed, dried over Na2SO4 and evaporated. [0054] A mixture composed of 5.6 g of potassium carbonate, 2.2 g of the above amine in 100 mL of acetone and 4 g of 3-(3-iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one is then refluxed for 18 hours. [0055] The solvent is evaporated off in vacuo, and the residue is taken up in ethyl acetate and then extracted with 3N hydrochloric acid. [0056] The aqueous phase separated off is brought to basic pH using sodium hydroxide and is then extracted with ethyl acetate. After washing until neutral and drying over MgSO4, evaporation in vacuo is carried out to obtain 4.5 g of an oil which is purified on a silica column using a mixture of dichloromethane/methanol (90/10) as eluant. [0057] Yield=64%

The synthetic route of 148870-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LES LABORATOIRES SERVIER; CARRANZA, Maria Del Pilar; GARCIA ARANDA, Maria Isabel; GONZALEZ, Jose Lorenzo; SANCHEZ, Frederic; US2014/163220; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 620621-48-9, These common heterocyclic compound, 620621-48-9, name is Methyl 2-chloro-5-iodobenzoate, 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.

Intermediate 2: Methyl 2-chloro-5-pyridin-2-ylbenzoate; A suspension of methyl 2-chloro-5-iodobenzoate (8.0 g, 27 mmol), 2- pyridineboronic acid N-phenyldiethanolamine ester (14.5 g, 54 mmol), palladium acetate (0.30 g, 1.35 mmol), potassium carbonate (7.46 g, 54.0 mmol), triphenylphosphine (1.42 g, 5.4 mmol) and copper iodide (2.06 g, 10.8 mmol) in THF (100 mL) was heated at 65 0C overnight under nitrogen. The reaction mixture was cooled, filtered through CeliteR and concentrated in vacuo, then the residue was suspended in DCM (250 mL) and filtered through Celite. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with EtOAc/isohexane (0 – 50%) to give the title compound as a solid (3.0 g, 49%):^ NMR 53.90 (3H, s), 7.39 – 7.43 (IH, m), 7.69 (IH, d), 7.89 – 7.95 (IH, m), 8.05 (IH, d), 8.24 – 8.28 (IH, m), 8.54 (IH, d), 8.68 – 8.70 (IH, m);MS 248.

The synthetic route of 620621-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/47558; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com