Category: iodides-buliding-blocks

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. 19094-56-5 name is 2-Chloro-5-iodobenzoic 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. 19094-56-5

[0249] A 250 mL of 4-necked flask equipped with thermometer and mechanical stirring was charged with NaBH4 (4.16 g, 0.11 mol) and THF (60 mL) under argon. After cooling to 0-5 C with stirring, a solution of iodine in THF (12.7 g I2 in 25 mL THF) was added slowly dropwise over 30 min and the reaction temperature was maintained below 10 C. After the addition was completed, a solution of 2-chloro-5-iodobenzoic acid (15.0 g, 50 mmol) in THF (20 mL) was added dropwise over 30 min and kept the reaction temperature below 10 C. After stirring for another 3 h at 20-25 C, the reaction mixture was heated to reflux for additional 16 h and monitored by TLC (PE/EA=1 : 1, Rf = 0.2). The mixture was cooled to 20-25 C and poured into ice water (100 mL), extracted with ethyl acetate (2 x 100 mL), washed with water (2 x 100 mL), brine (100 mL), concentrated and the residue was purified by flash chromatography (PE:EA=20: 1 as eluant, 200 mL) to give an off-white solid. Yield: 10.0 g (70%) MS ESI (m/z): 269 [M+l]+.

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

Reference:
Patent; THERACOS, INC.; XU, Baihua; LV, Binhua; XU, Ge; SEED, Brian; ROBERGE, Jacques; WO2013/152654; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common compound: 116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 116632-39-4

In N2Gas purification system, the compound G dissolved in a solution of tetrahydrofuran and toluene (5: 1), Compound H-1 (0.9 equiv) was added.Potassium carbonate (4.4 eq.) Was dissolved in deionized water was added Pd (0.05 eq.).The mixture was refluxed and stirred for 24 hours at the temperature 80 .After completion of the reaction, the mixture was extracted with organic solvent, and removing the organic solvent.The resultant was passed through the column to obtain Compound I-1

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, 116632-39-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG Display Co., Ltd.; Liang, Zhonghuan; Yin, Jiongchen; Lu, Xiaozhen; Yin, Dawei; Shen, Renai; Jin, Zunyan; (39 pag.)CN105524071; (2016); 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. 624-76-0, name is 2-Iodoethanol, This compound has unique chemical properties. The synthetic route is as follows., 624-76-0

A solution of 2,3,3-trimethyl-3H-indole (1 ml, 6.3 mmol) and 2-iodoethanol (0.56 ml, 8.8 mmol) in MeCN (4 mL) was refluxed for 1 day. After being cooled to r.t., the reaction mixture was suspended in hexane, and the precipitated solid was sonicated and filtered. A part of the obtained purple solid (53 mg out of 1.37 g) was dissolved in 1N KOH (2 mL) and stirred at r.t. for 30 min. After extraction with ether, the organic layer was evaporated to afford 4 as yellow oil, which was used for the next reaction without further purification. A solution of 5-nitrososalicylaldehyde (38 mg, 0.23 mmol) and the obtained 4 in EtOH (5 mL) was refluxed for 4 hours. The mixture was evaporated and purified by column chromatography (silica gel; eluent, hexane_AcOEt=1:1) to afford purple crystal 5 (56 mg, 66% based on 2,3,3-trimethyl-3H-indole). MS(EI): 352(M+, 15), 337(5), 321(9), 83(100); HRMS(EI): M+352.1411 (calc.352.1423); 1H NMR(CDCl3) delta1.20 (s, 3H), 1.30 (s, 3H), 3.34 (ddd, J=5.1, 5.1, 14.7 Hz, 1H), 3.47 (ddd, J=5.5, 7.3, 14.7 Hz, 1H), 3.69-3.82 (m, 2H), 5.89 (d, J=10.5 Hz, 1H), 6.67 (d, J=7.5 Hz, 1H), 6.77 (d, J=8.5 Hz, 1H), 6.90 (dd, J=7.5, 7.5 Hz, 1H), 6.91 (d, J=10.5 Hz, 1H), 7.10 (dd, J=1.1, 7.5 Hz, 1H), 7.50 (ddd, J=1.1, 7.5, 7.5 Hz, 1H), 8.00 (d, J=2.5, 1H), 8.03 (dd, J=2.5, 8.5 Hz, 1H).

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; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2007/195309; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, 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. 624-75-9

The compound obtained in Example 21 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours by heating. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and to the residue were added water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of [4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile and [4-(2-chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile as yellow oil. These two regioisomers (4.78 g, 92%) were used in the next reaction step without separation.[4-(2-Chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.29 (s, 3H), 3.71 (s, 3H), 5.19 (s, 2H), 6.73 (s, 1H), 6.75 (s, 1H), 6.85 (s, 1H), 7.06 (d, J=4.4 Hz, 1H), 7.26 (s, 1H), 7.79 (s, 1H), 8.24 (d, J=4.8 Hz, 1H); 13C NMR (CDCl3) delta 21.53, 39.97, 55.29, 110.91, 111.12, 113.65, 115.67, 118.75, 121.59, 121.65, 122.78, 130.58, 132.37, 140.16, 143.28, 149.68, 151.45, 151.79, 159.71, 162.33.[4-(2-Chloropyridin-4-yl)-5-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl]acetonitrile: 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.83 (s, 3H), 4.94 (s, 2H), 6.63 (s, 1H), 6.74 (s, 1H), 6.92-6.96 (m, 2H), 7.19 (s, 1H), 7.93 (s, 1H), 8.17 (d, J=5.2 Hz, 1H); 13C NMR (CDCl3) delta 21.56, 37.78, 55.48, 112.15, 113.91, 117.08, 118.16, 119.88, 121.36, 122.48, 128.46, 139.57, 141.60, 142.19, 142.85, 149.78, 151.95, 160.48.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 22 (300 mg, 0.89 mmol), 3-pyridineboronic acid (0.13 g, 1.06 mmol), dichlorobis(triphenylphosphine)palladium (II) (31 mg, 0.04 mmol) and potassium carbonate (130 mg, 0.89 mmol), and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL¡Á3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 2:1, v/v): (62 mg, 55%); m.p. 81-82 C.; 1H NMR (CDCl3) delta 2.39 (s, 3H), 3.80 (s, 3H), 4.95 (s, 2H), 6.73 (s, 1H), 6.80 (s, 1H), 6.94 (s, 1H), 7.11 (d, J=5.0 Hz, 1H), 7.34 (dd, J=3.0, 4.8 Hz, 1H), 7.54 (s, 1H), 8.00 (s, 1H), 8.15 (d, J=7.8 Hz, 1H), 8.54 (d, J=5.1 Hz, 1H), 8.60 (d, J=4.4 Hz, 1H), 8.89 (s, 1H); 13C NMR (CDCl3) delta 21.62, 37.79, 55.50, 112.38, 114.08, 116.81, 118.15, 119.21, 120.35, 122.59, 123.59, 128.90, 134.30, 134.78, 139.57, 140.71, 141.57, 141.97, 148.02, 149.92, 150.34, 154.99, 160.48.

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 624-75-9.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 2401-21-0, name is 1,2-Dichloro-3-iodobenzene, 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 2401-21-0, 2401-21-0

J. 17alpha-Chloro-17beta-Benzylsulfinyl-1,4-Androstadiene-3-One In a manner similar to that described in Example 2A, react 0.47 gm. of 17alpha-benzylthio-1,4-androstadiene-3-one, 19.2 ml. of pyridine, 4.8 ml. of water and 0.988 gm. of iodobenzene dichloride. Maintain the reaction at -40¡ã C. for 72 hours. Purify the residue by utilizing thin layer silica gel chromatography, developing with chloroform/ethyl acetate (2:1) and eluding with ethyl acetate to obtain the title compound; nmr (CDCl3) delta 1.23 (C10 and C13 –CH3, s), 4.03 (CH2 phi, dd), 6.08 (C4 –H, d), 6.23 (C2 –H, dd), 7.05 (C1 –H, d), 7.35 (phi, s).

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, 1,2-Dichloro-3-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Schering Corporation; US4183924; (1980); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

19094-56-5, A common compound: 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a stirred suspension of 2-chloro-5-iodobenzoic acid(5.65 g, 0.02 mol) in CH2Cl2(20 mL) was added oxalylchloride(1.80 mL, 0.021 mol) and DMF(0.02 mL). Theresulting mixture was stirred for 4 h at room temperature.The mixture was concentrated, and the residual colorlesssolid was dissolved in CH2Cl2(40 mL). To this solutionwere added corresponding substituted benzene(0.02 mol)and then AlCl3(2.75 g, 0.021 mol) portionwise so that thetemperature did not exceed 0 ¡ãC. After being stirred at 10?20 ¡ãC for 3 h, the mixture was poured into ice water andextracted with CH2Cl2 three times. The combined organiclayers were washed with 1M HCl, water, and brine, thendried over MgSO4 and concentrated. The residual solid wascrystallized from ethanol to give as white solid.According to this procedure the following compoundswere prepared. (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone (1a)White solid, yield 92percent, m.p. 69?70 ¡ãC. 1H NMR (400MHz,DMSO-d6): delta 7.38?7.40(m, 2H), 7.41(d, J=8.0 Hz, 1H), 7.82(dd, J=2.4 Hz, 8.0 Hz, 2H), 7.90(d, J=2.4 Hz, 1H), 7.92?7.95(m, 1H). 13C NMR (100MHz, DMSO-d6): delta 116.19,129.47, 131.65, 132.1, 132.65, 136.78, 139.69, 140.20,164.54, 166.56, 191.36. HRMS (ESI) m/z (pos):382.91890C13H7ClFIONa [M+Na]+(calcd. 382.91118).

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-iodobenzoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hu, Shengquan; Sun, Wuji; Wang, Yeming; Yan, Hong; Medicinal Chemistry Research; vol. 28; 4; (2019); p. 465 – 472;,
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. 135050-44-1, name is 3-Chloro-4-iodoaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 135050-44-1

EXAMPLE 24 (3-Chloro-4-iodo-phenyl)-carbamic acid tert-butyl ester To a solution of 3-chloro4-iodoaniline (20.2 g) in tetrahydrofuran (200 ml) was added di-tert-butyl dicarbonate (39 g) and N,N-diisopropylethylamine (30.9 g). The mixture was heated to reflux for approximately 24 hours, cooled and the solvent removed by evaporation in vacuo. The resulting residue was dissolved in ethyl acetate (450 ml), washed twice with of 5% aqueous hydrochloric acid, once with saturated aqueous sodium bicarbonate, once with water, once with saturated sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation in vacuo, and trituration of the product with hexanes gave the product as a crystalline solid. MS (-ES) m/z: 352 (M-H)-. Additional purification was accomplished by recrystallization from hot hexanes.

The synthetic route of 135050-44-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US5932745; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

619-58-9, The chemical industry reduces the impact on the environment during synthesis 619-58-9, name is 4-Iodobenzoic acid, I believe this compound will play a more active role in future production and life.

4-lodobenzoic acid (10 g, 40.3 mmol) was dissolved in dry toluene (100 ml, dried over mol. sieves). The solution was heated to 70 C under a flow of nitrogen. A solution of lambda/,lambda/-dimethylformamide di-tert-butyl acetal (24.6 g, 121 mmol) in toluene (25 mL) was added over ca. 30 min. The reaction was mixed for 16 h. At some point the heating unit failed, so the reaction cooled from 70 C to rt. The solution was heated to 70 C for and mixed for 5 h. The sample was concentrated under vacuum, and AcOEt (400 ml) was added. The solution was then washed with 1 :1 sat. NaHCO3/water (150 ml), and sat. NaHCO3, water and sat. NaCI (75 mL each). The organic phase was dried (MgSO4) and concentrated under vacuum to yield light brown oil. HPLC-MS m/z: 327 (M+23).1H-NMR (CDCI3, 400 MHz) delta 7.77 (d, 2H), 7.69 (d, 2H), 1.58 (s, 9H).

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

Reference:
Patent; NOVO NORDISK A/S; WO2007/128817; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

914225-70-0, A common compound: 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a 500 mL reactor, 5-fluoro-2-iodoacetophenone (39.6 g, 150 mmol) was added.Glyoxylic acid monohydrate (13.9 g, 151 mmol), heating the reaction and distilling off water (95 , 0.1 Mpa) under reduced pressure for 3 hours.The reaction mixture was cooled to room temperature, 5% aqueous potassium carbonate solution (300 mL), and extracted twice with ethyl acetate,After 200 mL of water, the aqueous layer was acidified (10% hydrochloric acid, 300 mL), and then extracted twice with ethyl acetate.200 mL each time, the organic phase was combined, washed with brine and dried over anhydrous sodium sulfate.The solvent was removed under reduced pressure to give an orange solid.The solid was dissolved in glacial acetic acid (50 mL), concentrated hydrochloric acid (36%, 5mL).Acetic acid under reduced pressure, the residue was extracted (300 mL) with ethyl acetate, washed with brine three times,100 mL each time, the organic phase was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.To give the desired product (26.89g, 56%) as a yellow solid, M.P.146 degrees.

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-(5-Fluoro-2-iodophenyl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shanghai Health Medical School; Huang Gang; Li Bin; (101 pag.)CN109705124; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

52548-14-8, These common heterocyclic compound, 52548-14-8, name is 2-Iodo-5-methylbenzoic acid, 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.

To 2-iodo-5-methylbenzoic acid (1.5 g, 5.72 mmol), copper(I) iodide (1.090 g, 5.72 mmol) and (lR,2R)-N,N’-dimethyl-l,2-cyclohexanediamine (0.814 g, 5.72 mmol) was added DMF (10 ml) under nitrogen and then 2H-l,2,3-triazole (0.474 g, 6.87 mmol). The reaction mixture was heated at 120 C at the microwave Personal Chemistry for 15 minutes. UPLC- MS monitor showed that the reaction was complete. After cooling at room temperature water was added and the aqueous washed with EtOAc. Then the aqueous acidified to pH =1 with aqueous 1 M HC1 and extracted with EtOAc. The phases were separated on a hydrophobic frit, the combined organic solvent was removed to give the crude product (2.4 g).The crude compound was purified by silica gel chromatography (SNAP KP-Sil lOOg cartridge) eluted with 5 CV of a mobile phase prepared with DCM (959.04 ml), acetic acid (0.96 ml) and MeOH (40 ml). The evaporation of proper fractions gave a yellow oil which was triturated with toluene (4 x 50 ml) and the title compound D44 was obtained as yellow solid (540 mg).UPLC (Basic GEN QC): rt = 0.35 minutes, peak observed: 204 (M+l) Ci0H9N3O2 requires: 203.1H NMR (400 MHz, DMSO-d6) delta ppm 2.44 (s, 3 H) 7.52 (dd, 1 H) 7.59 (s, 1 H) 7.64 (d, 1 H) 8.06 (s, 2 H).

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 52548-14-8.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com