Month: April 2021

Synthetic Route of 58313-23-8, 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. 58313-23-8, name is Ethyl-3-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a dried sealed vessel was added 1,2,3,4-tetrahydroisoquinoline (5 mL, 40 mmol), anhydrous K2CO3 (8.34 g,60 mmol), CuI (0.8 g, 4 mmol), L-Proline (0.92 g, 8 mmol), ethyl 6-bromopicolinate (4.32 g, 20 mmol), and DMSO (25 mL). Then themixture was stirred at 80 C for 16 h under N2 environment. Aftercooling to room temperature, water (100 mL) was added andextracted with EtOAc. Then, the combined organic layer was driedover MgSO4, filtered, and concentrated. The residue was purified bysilica gel flash chromatography (hexane/EtOAc = 5/1) to providecompound 14 as a white oil (3.94 g, 70%).

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

Reference:
Article; Fang, Yuying; Zhou, Huihao; Gu, Qiong; Xu, Jun; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 133 – 145;,
Iodide – Wikipedia,
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Reference of 5876-51-7, The chemical industry reduces the impact on the environment during synthesis 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, I believe this compound will play a more active role in future production and life.

A 20 ml vial charged with 1-iodo-3,4-methylenedioxybenzene (0.13 ml, 1.001mmol), (R)-pyrrolidin-2-ylmethanol (0.11 ml, 1.115 mmol), copper (1) iodide (0.153g,0.803 mmol) and 2-propanol (3.5 ml) was evacuated and backfilled with nitrogen four times and cooled at 0C in an ice-water bath. Powdered sodium hydroxide (0.08 1 g, 2.025 mmol) was then added and the mixture was stirred for 10 minutes at 0C (solution became purple) and 16 hours at 90C (solution became orange). The reaction mixture wascooled down to room temperature, diluted with ethyl acetate, washed with water, and the water layer was back extracted twice with ethyl acetate. Combined organic layers were washed once with saturated aqueous NaHCO3 solution, once with water, once with brine, dried on anhydrous Na2SO4, filtrated and concentrated. The residue was purified on ISCO using a 25g Innoflash column (Hex/EtOAc) to give title material (0.166 g, 75%) as yellowish oil. LC (Method A): 0.886 mm. MS (APCI) calcd for C12H16N03 [M+H] rn/z 222.11, found 222.2. ?H NMR (400 MHz, acetone-d6) oe ppm 6.67 (d, J 8.2 Hz, 1 H),6.31 (d, J = 2.3 Hz, 1 H), 6.04 (dd, J = 2.5, 8.4 Hz, 1 H), 5.83 (d, J = 1.2 Hz, 1 H), 5.82 (d,J = 0.8 Hz, 1 H), 3.74 (t, J 5.7 Hz, 1 H), 3.69 – 3.58 (m, 2 H), 3.41 – 3.29 (m, 2 H), 3.02 (dt, J = 5.9, 9.0 Hz, 1 H), 2.12 – 1.87 (m, 4 H).

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-Iodobenzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITE DE MONTREAL; MARTEL, Alain; TREMBLAY, Francois; (207 pag.)WO2017/66863; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 31970-26-0, 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. 31970-26-0, name is 1-(4-Iodophenyl)propan-1-one belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Finely powdered cuprous bromide (20.21 g, 91 mmol) was suspended in ethyl acetate (30 mL) and heated to reflux. A solution of ketone (14 g, 54 mmol) in chloroform (30 mL) was added dropwise over 10 minutes. After refluxing for 7 hours, the reaction was left to cool overnight and filtered through Celite. The filtrate was washed with saturated aqueous sodium bicarbonate (2¡Á50 mL) and brine (50 mL), dried over magnesium sulfate and concentrated under reduced pressure. Recrystallization from hexane afforded a pale yellow solid. mp 76 C. Yield 12.2 g (66%). 1H NMR (CDCl3) delta7.83 (d, 2H), 7.72 (d, 2H), 5.21 (q, 2H), 1.87 (d, 3H). MI=338. IR (Liq film) cm-1 1677. Calculated for C9H8BrIO: C, 31.9%, H, 2.38%. Found: C, 32.2%, H, 2.5%.

The synthetic route of 1-(4-Iodophenyl)propan-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tisdell, Francis Eugene; Bis, Scott Jerome; Hedge, Vidyadhar Babu; Martin, Timothy Patrick; Perreault, Denise Marie; Yap, Maurice Chee Hoong; Guenthenspberger, Katherine Anne; Dripps, James Edwin; Gifford, James Michael; Schoonover, Joe Raymond; Karr, Laura Lee; Dintenfass, Leonard Paul; Neese, Paul Allen; US2004/6108; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 627-32-7, name is 3-Iodo-1-propanol, 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 627-32-7, Computed Properties of C3H7IO

To a solution of 12 (221 mg, 0.42 mmol) in MeOH (5 mL) was added KOH (26 mg, 0.46 mmol). The mixture was stirred at room temperature for 30 min, and then concentrated under reduced pressure to give a potassium salt, which was dissolved in DMF (5 mL) and treated with 3-iodo-1-propanol (52 muL, 0.55 mmol). After stirring at room temperature for 5 h, the mixture was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 (20 mL) and extracted with 1 M HCl and brine. The organic phase was dried over MgSO4, concentrated under reduced pressure, and purified by flash chromatography on a silica gel column (EtOAc/hexane = 1:1) to afford ester 13 (137 mg, 55%). C28H48N4O9; colorless solid, mp 95-97 C; TLC (EtOAc/hexane = 3:1) Rf = 0.28; inlMMLBox -68.0 (c 1.4, CHCl3); IR numax (neat) 3278, 2970, 2932, 1724, 1643, 1610, 1252, 1144, 1055 cm-1; 1H NMR (400 MHz, CDCl3) delta 11.33 (1H, s), 8.58 (1H, d, J = 8.4 Hz), 6.75 (1H, s), 6.51 (1H, d, J = 8.8 Hz), 4.34-4.28 (1H, m), 4.26-4.21 (2H, m), 4.07 (1H, m), 3.97 (1H, d, J = 7.6 Hz), 3.64 (2H, t, J = 6.4 Hz), 3.29 (1H, t, J = 5.6 Hz), 2.73-2.68 (1H, m), 2.33 (1H, dd, J = 17.6, 9.2 Hz), 1.88-1.82 (5H, m), 1.50-1.43 (22H, m), 0.86-0.78 (6H, m); 13C NMR (100 MHz, CDCl3) delta 170.0, 166.0, 162.9, 156.7, 152.3, 138.4, 128.2, 83.5, 82.7, 79.5, 76.1, 61.8, 58.9, 54.3, 48.2, 31.8, 30.7, 28.4 (3¡Á), 28.1 (3¡Á), 26.1, 25.8, 23.4, 9.7, 9.4; ESI-HRMS calcd for C28H48N4O9: 585.3496, found: m/z 585.3500 [M+H]+.

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

Reference:
Article; Liu, Kung-Cheng; Lee, Pei-Shan; Wang, Shi-Yun; Cheng, Yih-Shyun E.; Fang, Jim-Min; Wong, Chi-Huey; Bioorganic and Medicinal Chemistry; vol. 19; 16; (2011); p. 4796 – 4802;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 76801-93-9, 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 76801-93-9 as follows.

EXAMPLE 1 ; Compound B is suspended in a mixture of acetic anhydride and acetic acid (5-15 v/v % acetic acid, about 1.5-3.0 liter of acetic anhydride and acetic acid combined per kg of Compound B) in a continuous facility as described in Figure 1. The acetylation is performed in two steps in continuous stirred tank reactors at different temperatures (55 and 120C) with residence times from about 0 to 2 hours. Excess acetic acid and acetic anhydride are removed by distillation in a continuous evaporation system. The viscous residue is diluted with methanol (which reacts with residual acetic anhydride and also with O-acetyl groups deriving from Compound B), and the resulting methyl acetate is continuously removed by atmospheric distillation at about 50-60C. The HPLC purity of the resulting crude reaction mixture is about 98 % with respect to Compound A.

According to the analysis of related databases, 76801-93-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GE Healthcare AS; EP2281814; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 41252-95-3,Some common heterocyclic compound, 41252-95-3, name is 1-Chloro-4-iodo-2-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.

Preparation of 6-iodo-2-oxindole from 2-chloro-5-iodonitrobenzene and diethyl malonate Without Isolation of Intermediates To a jacketed reactor, N,N-dimethylacetamide (DMAc) (120 mL) and sodium ethylate (NaOEt) powder (12.1 g) is charged at 20 C. Diethylmalonate (28.8 g) is added dropwise into the above mixture while keeping internal temperature at around 10 C. After finishing addition, warm up the mixture to 20 C., and continue to stir for another 10 minutes. Then, 2-chloro-5-iodonitrobenzene (17 g) is added in one portion, and heat the mixture to 78 C. and stir for usually at least 2.5 hours until process monitor shows almost complete conversion. The resulting mixture is cooled down to 20 C., and it is quenched by 2 N cold aq. HCl solution (180 mL). The bottom yellow oil was transferred to a jacket reactor with ethanol (92 mL) in it. Then, to the above solution the first portion of SnCl2.2H2O (30 g) powder is added, and the resulting mixture is heated to 70 C. and stirred for 1 hour. The second portion of SnCl2.2H2O (30 g) is added, the mixture is stirred usually at least 0.5 hour until process monitor shows almost complete conversion. Then, heat the resulting mixture to 80 C. and add 36% aq. HCl solution (60 mL) during 0.5 hour. The mixture is stirred for at least 2.5 hours until process monitor shows almost complete conversion. Then, to the mixture water (90 mL) is added and the resulting mixture is cooled down to 20 C. Collect the solid by filtration and wash the solid with water (250 mL) to afford the crude 6-iodo-2-oxindole. Then, it is purified by crystallization with acetic acid (HOAc) (110 mL), and followed by washing with 3 N aq. HCl solution (80 mL) to afford the 6-iodo-2-oxindole in 53% yield and 99% HPLC purity (Rt=7.45 min). 1H NMR (400 MHz, DMSO) delta10.42 (S, 1H), 7.29-7.27 (dd, J=8.0, 1.6 Hz, 1H,), 7.11 (d, J=1.6 Hz, 1H), 7.02-7.00 (d, J=8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) delta 175.9, 145.3, 129.6, 126.4, 125.7, 117.4, 92.2, 35.4; MS (ESI): m/z 260.1 (M+1).

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

Reference:
Patent; Boehringer Ingelheim International GmbH; SHI, Wenjian; Song, Yanli; Bao, Yuhui; Lu, Jun; Huang, Yao; Weber, Dirk; US2014/66634; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, 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. name: 2-Iodo-1,3-dimethylbenzene

General procedure: A mixture of Cu0 powder (Sigma-Aldrich, <425mum, 99.5% trace metals basis, 0.095mg, 0.015mmol, 3-mol%), anhydrous K3PO4 (0.75mmol), 2-mercaptoimidazole/sulfur-containing azoles (0.5mmol), DMSO (0.2mL) and aryl halide (0.75mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100C for 24h. The heterogeneous mixture was subsequently cooled to room temperature and diluted with 4.0mL dichloromethane. The combined organic extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was loaded onto the column using minimal amounts of dichloromethane and was purified by silica-gel column chromatography to afford the S-arylated product. The identity and purity of products was confirmed by 1H and 13C NMR spectroscopic analys. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 608-28-6, its application will become more common. Reference:
Article; Tan, Bryan Yong-Hao; Teo, Yong-Chua; Tetrahedron; vol. 72; 42; (2016); p. 6646 – 6653;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 4387-36-4, A common heterocyclic compound, 4387-36-4, name is 2-Iodobenzonitrile, molecular formula is C7H4IN, 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.

The specific reaction operation is:At room temperature,Add 100 mmol of the compound of the above formula (II), 200 mmol of the compound of the above formula (III), 0.4 mmol of palladium acetate, to an appropriate amount of the organic solvent N,N-dimethylacetamide (DMA).150 mmol of tetra-n-butylammonium bromide and 150 mmol of sodium carbonate,Then stir to raise the temperature to 120 ¡ã C,And stirring the reaction at this temperature for 15 hours;After the reaction was completed, the reaction mixture was poured into a sufficient amount of ethyl acetate.After washing with saturated brine, the organic layer and the aqueous layer were separated.After the aqueous layer is sufficiently extracted with ethyl acetate,The combined organic layers (i.e., the organic layer washed with saturated brine and organic layer extracted from ethyl acetate) were dried over anhydrous Na2SO?The residue was eluted by flash column chromatography (a mixture of petroleum ether and ethyl acetate in a ratio of 8:1 as eluent).The eluent was collected and evaporated to remove the eluent.Thereby obtaining a compound of the above formula (I) as a white solid,The yield was 87.8percent.

The synthetic route of 4387-36-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wenzhou Medical University Affiliated The Second Hospital ? Wenzhou Medical University Affiliated Yuying Child Hospital; Wenzhou Medical University; Wang Zhiyi; Pan Chenwei; Chen Chan; Weng Jie; Wang Xianqin; Xu Tong; Wu He; (10 pag.)CN108250103; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 18698-96-9, A common heterocyclic compound, 18698-96-9, name is 2-(2-Iodophenyl)acetic acid, molecular formula is C8H7IO2, 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-(2-lodophenyl)acetic acid (5.00 g, 19.1 mmol) was placed into a reaction flask and dissolved in MeOH (150 mL). Sulfuric acid (250 pL) was added and reaction mixture was stirred and heated at 80 “C under nitrogen for 16 hours. The resulting mixture was cooled to room temperature and the volatiles removed by evaporation under reduced pressure. The residue was taken up in ethyl acetate (100 mL), washed with 10% NaHC03 (100 mL), dried (MgS04) and evaporated under reduced pressure to give the title compound (/9) (5.20g, 99%) as a clear liquid; 1H NMR (400 MHz, CDCI3) delta 7.85 (dd, J = 7.9, 1 .0 Hz, 1 H), 7.35 – 7.27 (m, 2H), 6.97 (ddd, J = 7.9, 7.0, 2. Hz, 1 H), 3.81 (s, 2H), 3.72 (s, 3H).

The synthetic route of 18698-96-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LIMITED; HOLMES, Ian, Peter; BERGMAN, Ylva; LUNNISS, Gillian Elizabeth; NIKAC, Marica; CHOI, Neil; HEMLEY, Catherine Fae; WALKER, Scott Raymond; FOITZIK, Richard Charles; GANAME, Danny; LESSENE, Romina; WO2012/110773; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 14452-30-3, name is 1-(3-Iodophenyl)ethanone, 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 14452-30-3, Recommanded Product: 14452-30-3

To a stirred solution of daST (2.25 mL, 12.19 mmol) was added meOH (20 uL), and then 3′- iodoacetophenone (2.0 g, 8.13 mmol) dropwise. The resulted mixture was heated to 50 oc for 16 h under nitrogen atmosphere. after cooling to room temperature, the reaction mixture was poured into sat. aq. NaHcO3 (50 mL) and extracted with EtOac (30 mL x 2). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na₂SO₄, filtered and concentrated in vacuo. The crude rESIdue was purified by silica gel chromatography (eluting with petroleum ether) to give the title compound (144 mg, 7%) as colorless oil.1H NMR (400 MHz, CDCl3) d 7.86 (s, 1H) 7.73 (d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.0 Hz, 1H) 7.18 – 7.16 (m, 1H) 1.91(t, J = 18.0 Hz, 3H).

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; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; MCKERRALL, Steven; BEVERIDGE, Ramsay; LAI, Kwong Wah; BERGERON, Philippe; (190 pag.)WO2019/226687; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com