Category: iodides-buliding-blocks

Some common heterocyclic compound, 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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. Safety of 1-Iodo-3-(trifluoromethyl)benzene

The mixture of Intermediate-51a (150mg, 0.45mmol), l-iodo-3(trifluoromethyl)benzene (0.18g,0.68 mmol) and CS2CO3 (0.22 g, 0.68 mmol) in toluene (7mL) was degassed for 15 min by purging nitrogen followed by addition of bis (tri-tert-butylphosphine palladium(O) (11.53mg, 0.023 mmol) and tris dibenzylidene acetone dipalladium (0)(20.66mg,0.023 mmol). The reaction mixture was heated to 110C and further maintained for 20 hr at the same temperature. The reaction mixture was cooled to room temperature and progress of reaction monitored by TLC. The mixture was diluted with ethyl acetate, filtered through celite and concentrated under vacuum to give crude compound. This crude compound was further purified by flash chromatography using a mixture of 20% ethylacetate in hexane (0.17g, 79%).Ethereal HCl (2 mL) was added and stirred for 10 min. The solvent was evaporated and solid washed by diethyl ether (2 mL) followed by «-pentane (2 ml), dried to get HCl salt of title compound.m/z 477.2; *H NMR (400 MHz, DMSO-d6): delta 9.64 (bs, IH), 9.10 (bs, IH), 8.24 (d, 7=8.4 Hz, IH), 8.03 (t, 7=8.8 Hz, 2H), 7.89 (d, 7=7.2 Hz, IH), 7.63-7.48 (m, 6H), 7.37(d, 7=7.6 Hz, IH), 6.93 (d, 7=7.2 Hz, IH), 6.80-6.77 (m, 3H), 5.34 (m, lH), 4.28 (m, 1H),3.85 (m, lH), 3.47-3.10 (m, 3H), 2.03 (m, 2H), 1.67 (d, 7=6.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 401-81-0, its application will become more common.

Reference:
Patent; LUPIN LIMITED; SHUKLA, Manojkumar, Ramprasad; ANKUSH, Sarde, Gangaram; VIPUL, Pachpute, Dilip; KULKARNI, Sanjeev, Anant; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/127385; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

3032-81-3, name is 1,3-Dichloro-5-iodobenzene, 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: 1,3-Dichloro-5-iodobenzene

General procedure: A suspension of coupling substrate 2d?g (1 equiv), copper(I) iodide (0.5 equiv), cesium carbonate (2 equiv), and the corresponding aryl halide (1 equiv) in dioxane was placed under a nitrogen atmosphere. The coupling ligand DMEDA (1 equiv) was added dropwise by using a syringe and the mixture was then stirred at r.t. for various periods of time (2.5?48 h). At the end of the reaction, all insoluble salts deposited after cooling at r.t. were collected by filtration then washed with dichloromethane. The resulting filtrate was concentrated in vacuo and the residue was partitioned between water and dichloromethane. The organic layer was dried over MgSO4 and evaporated to dryness. The reaction residues were recrystallized or purified by chromatography on silica gel column to afford pure compounds 36?39.

The synthetic route of 3032-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baudelet, Davy; Daich, Adam; Rigo, Benoit; Lipka, Emmanuelle; Gautret, Philippe; Homerin, Germain; Claverie, Christelle; Rousseau, Jolanta; Abuhaie, Cristina-Maria; Ghinet, Alina; Synthesis; vol. 48; 14; (2016); p. 2226 – 2244;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 328-73-4,Some common heterocyclic compound, 328-73-4, name is 1-Iodo-3,5-bis(trifluoromethyl)benzene, molecular formula is C8H3F6I, 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.

A 2-dram vial equipped with a magnetic stir bar was charged with the amide substrate (36.5 mg, 0.10 mmol), Pd(OAc)2 (2.2 mg, 10 molpercent) , ligand L19 (4.1 mg, 20 molpercent), AgOAc (50 mg, 0.30 mmol) and norbornene (14.1 mg, 0.15 mmol). Aryl iodide (0.30 mmol) and 1.0 mL of t-butyl methyl ether were then added to the mixture. The vial was capped and closed tightly. The mixture was stirred at 95 °C for 12 hours . After cooling to room temperature, the mixture was passed through a pad of Celite® with ethyl acetate as the eluent to remove all the insoluble compounds. The resulting solution was concentrated, and the residual mixture was dissolved with a minimal amount of acetone and loaded onto a preparative TLC plate. The pure product was then isolated by preparative TLC with ethyl acetate and hexanes as the eluent. 2- { 5- [2- (Me hoxycarbonyl) henyl] -2-methylphenyl } – N- [2 , 3 , 5 , 6-tetrafluoro-4- (trifluoromethyl) phenyl] – ace amide Preparative TLC using hexanes/EtOAc (4/1) as the eluent provided the pure product as a white solid (64percent yield). NMR (600 MHz, acetone-d6) delta 9.54 (br, 1H, N-H) , 7.75 (d, J = 7.6 Hz, 1H) , 7.59 (t, J = 7.6 Hz, 1H) , 7.46 (t, J = 7.6 Hz, 1H) , 7.44 (d, J = 7.6 Hz, 1H) , 7.30 (d, J = 1.4 Hz, 1H) , 7.27 (d, J = 7.7 Hz, 1H) , 7.17 (dd, J = 7.7, 1.4 Hz, 1H) , 3.97 (s, 2H) , 3.60 (s, 3H) , 2.41 (s, 3H) ; 13C NMR (150 MHz, acetone-d6) delta 169.70, 169.43, 142.44, 139.82, 137.14, 134.19, 132.37, 132.01, 131.35, 131.26, 130.96, 130.31, 128.03, 127.96, 52.15, 41.17, 19.40. HRMS (ESI-TOF) m/z Calcd for C24Hi7F7N03+ [M+H] + 500.1091, found 500.1090. 6 Equivalents of Arl was used, and AgOAc was replaced by AgOPiv (3 eq. ) in this reaction. Column chromatography using hexanes/EtOAc (4/1) as the eluent provided the pure product as a white solid (76percent yield). XH NMR (400 MHz, acetone-d6) delta 9.62 (br, 1H, N-H) , 8.28 (s, 2H) , 8.02 (s, 1H) , 7.86 (d, J = 2.0 Hz, 1H) , 7.71 (dd, J = 8.0, 2.0 Hz, 1H) , 7.40 (d, J = 8.0 Hz, 1H) , 4.06 (s, 2H) , 2.44 (s, 3H) ; 13C NMR (150 MHz, acetone-d6) delta 169.33, 144.09, 139.45, 136.35, 135.64, 132.65 (q, J = 33.0 Hz), 132.08, 130.11, 127.93, 127.00, 124.54 (q, J = 270.0 Hz), 121.43 (m) , 41.20, 19.40. HRMS (ESI-TOF) m/z Calcd for C24Hi3F13 O+ [M+H]+ 578.0784, found 578.0785.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Iodo-3,5-bis(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; YU, Jin-Quan; (107 pag.)WO2016/123361; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 128140-82-9, 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. 128140-82-9, name is 1-(Difluoromethoxy)-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenol A solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5 min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260. EXAMPLE 81Preparation of 2-Amino-5-[4-(difluoromethoxy)phenyl]-5-(3hydroxyphenyl)-3-methyl-3,5-dihydro-4H-imidazol-4-one Step a) 3-((4-(Difluoromethoxy)phenyl)ethynyl)phenolA solution of 4-(difluoromethoxy)phenyl iodide (4.70 g) in deoxygenated dimethylformamide was treated with trans-dichlorobis(triphenylphosphine) palladium(II) (244 mg) and copper(II) iodide 66 mg) followed by triethylamine (7.52 mL), stirred under a nitrogen atmosphere for 5 min., treated with 3-hydroxyphenyl acetylene (2.467 g), stirred under nitrogen atmosphere for 16 h, poured into ethyl acetate and was washed with 0.05 N HCl and water. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was chromatographed, silica gel, 40% ethyl acetate/hexane as eluent, to afford 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol as a tan solid, 5.40 g; 1H NMR (DMSO-d6): delta 9.64 (s, 1H), 7.56 (d, J=8.8 Hz, 2H), 7.27 (t, J=73.7 Hz, 1H), 7.17 (d, J=8.8 Hz, 2H), 7.16 (m, 1H), 6.94 (m, 1H), 6.86 (m, 1H), and 6.77 (m, 1H); MS (ES neg) m/z 260.

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-(Difluoromethoxy)-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; US2009/48320; (2009); 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. 696-41-3, name is 3-Iodobenzaldehyde, A new synthetic method of this compound is introduced below., Computed Properties of C7H5IO

Triethyl phosphonoacetate (9.21 g, 41.12 mmol) in tetrahydrofuran (65 mL) was treated with 2.5 M n-butyl lithium in hexanes (12.82 mL, 32.07 mmol) at -78 C. The resulting mixture was stirred for 10 min and added via a cannula to a pre-cooled solution at -78 C of 3-iodobenzaldehyde (4.77 g, 20.56 mmol) in tetrahydrofuran (20 mL). The resulting mixture was stirred at -78 C for 40 min and slowly warmed to ambient temperature for 45 min. The reaction was quenched with saturated aqueous NH4Cl (200 mL). The aqueous solution was extracted with diethyl ether. The resulting organic layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel chromatography (90:10 hexanes/ethyl acetate) to give 5.71 g (92%) of compound 1a as a yellow oil; 1H NMR (CDCl3) delta 1.32 (t, J = 7.1 Hz, 3H); 4.24 (q, J = 7.1 Hz, 2H); 6.39 (d, J = 16.0 Hz, 1H); 7.09 (dd, J = J’ = 7.8 Hz, 1H); 7.43-7.46 (m, 1H); 7.54 (d, J = 16.0 Hz, 1H); 7.64-7.69 (m, 1H); 7.83-7.86 (m, 1H).

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:
Article; Fabio, Karine; Guillon, Christophe; Lacey, Carl J.; Lu, Shi-Fang; Heindel, Ned D.; Ferris, Craig F.; Placzek, Michael; Jones, Graham; Brownstein, Michael J.; Simon, Neal G.; Bioorganic and Medicinal Chemistry; vol. 20; 3; (2012); p. 1337 – 1345;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

Example 7; [0055] Synthesis of 3-(benzyloxy)-1 -(3-iodopropyl)pyridin-2(1 H)-one(Compound 7); To a solution of 1 ,3-diiodopropane (7.1 ml_, 63 mmol) in tetrahydrofuran (50 ml_) was added 3-(benzyloxy)pyhdin-2(1 H)-one (1.28 g, 6.3 mmol) and Na2CO3 (0.67 g, 6.3 mmol). The mixture was then stirred at 70 0C for 1 day. Reaction progress was monitored by ES-MS. After ESMS showed essentially complete consumption of the starting material 3-(benzyloxy)pyhdin-2(1 H)-one, the reaction was stopped. Then the reaction mixture was filtered, concentrated, and subjected to flash column chromatography (eluent: hexane : ethylacetate 1 :1 ). Compound 7 was obtained (240 mg, 10% yield). Analysis: ES-MS (positive ion in MeOH/H2O): m/z = 370.2, ([M+H]+, calculated: 370.03).

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOARD OF SUPERVISORS OF LOUISIANA STATE UNIVERSITY AND ARGRICULTURAL AND MECHANICAL COLLEGE; WO2008/100907; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2974-94-9, 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. 2974-94-9 name is 1-Iodo-4-phenoxybenzene, 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.

Compound 4: 25 mL reaction flask was charged with 4-phenoxyiodobenzene (0.5 mmol), 3-ethoxyphenylboronic acid (0.75 mmol), sodium carbonate (1.0 mmol), and cesium hydroxide monohydrate (2.5 mmol), sodium iodide (0.25 mmol), pivalic acid (0.75 mmol), chloroform (1.5 mmol) and ethylene glycol (2.0 g). Reacted at 120 C for 24 h. Cool to room temperature, extract, the solvent was evaporated under reduced pressure and then purified by column chromatography to yield a yield of 92%.

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

Reference:
Patent; Nanjing Normal University; Han Wei; Xu Fangning; (15 pag.)CN108774122; (2018); A;,
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. 4897-68-1, name is 1-Bromo-2-iodo-4-methoxybenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 1-Bromo-2-iodo-4-methoxybenzene

GP-1 carried out, to an oven dried Schlenk tube under nitrogen atmosphere, were added allyl alcohol 6a (100 mg, 0.61 mmol), arylhalide 5b (228 mg, 0.73 mmol), Pd(OAc)2 (4.1 mg, 3 mol%), triethylamine (123 mg, 1.22 mmol) followed by dry acetonitrile (1 mL). The resulted reaction mixture was stirred for 24 h at 80 C. The reaction mixture was quenched with the aqueous NH4Cl solution and extracted with ethyl acetate (3 × 20 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification of the residue on a silica gel column chromatography (petroleum ether/ethyl acetate 92:8 to 85:15) eluent furnished the ketone 7ba (153 mg, 72%) as product. [TLC control Rf(6a)=0.50, Rf(7ba)=0.6, Rf(5b)=0.9 (petroleum ether/ethyl acetate 8:2, UV detection)]. IR (MIR-ATR, 4000-600 cm-1): nmax=3001, 2924, 2852, 1683, 1581, 1467, 1429, 1358, 1243, 1164, 1126, 1042, 1018, 872, 800, 772 cm-1. 1H NMR (CDCl3, 400 MHz): delta=7.55 (d, 1H, J=8.0 Hz, ArH), 7.50 (d, 1H, J=2.6 Hz, Ar-H), 7.42 (d, 1H, J=8.7 Hz, Ar-H), 7.35 (dd, 1H, J=8.0 and 8.0 Hz, ArH), 7.09 (dd, 1H, J=8.0 and 2.6 Hz, ArH), 6.85 (d, 1H, J=3.0 Hz, ArH), 6.64 (dd, 1H, J=8.7 and 3.0 Hz, ArH), 3.28 (t, 2H, J=8.0 Hz, ArCOCH2), 3.12 (t, 2H, J=8.0 Hz, ArCOCH2CH2) ppm. 13C NMR (CDCl3, 100 MHz): delta=198.8 (s, ArCO), 159.8 (s, ArC), 159.1 (s, ArC), 141.5 (s, ArC), 138.1 (s, ArC), 133.4 (d, ArCH), 129.6 (d, ArCH), 120.7 (d, ArCH), 119.7 (d, ArCH), 116.3 (d, ArCH), 114.7 (s, ArC), 113.7 (d, ArCH), 112.3 (d, ArCH), 55.5 (s, 2C, 2 × ArOCH3), 38.7 (t, ArCOCH2), 31.4 (t, ArCOCH2) ppm. HR-MS (APCI+) m/z calculated for [C17H18BrO3]+=[M+H]+: 349.0434; found: 349.0418.

The synthetic route of 4897-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suchand; Krishna; Venkat Ramulu; Dibyendu; Gopi Krishna Reddy; Mahendar; Satyanarayana; Tetrahedron Letters; vol. 53; 30; (2012); p. 3861 – 3864;,
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. 624-76-0, name is 2-Iodoethanol belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Iodoethanol

Production Example 235-1 Synthesis of 2-iodoethyl acetate 2-Iodoethanol (1.541 g, 8.96 mmol) was dissolved in dichloromethane (30 ml). To the solution, pyridine (1.54 ml, 17.92 mmol), N,N-dimethyl-4-aminopyridine (109 mg, 0.896 mmol), and acetic anhydride (2.54 ml, 26.88 mmol) were added, and the mixture was stirred at room temperature for 3 hours. After reaction, the organic layer was washed with 0.1M hydrochloric acid and a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over magnesium sulfate, and the solvent was distilled off to obtain the title compound (1.108 g, yield: 57.8%) as a yellow oil. 1H-NMR (400 MHz, DMSO-d6) delta: 2.10 (3H, s), 3.30 (2H, t, J=6.8 Hz), 4.33 (2H, t, J=6.8 Hz).

The synthetic route of 624-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kabushiki Kaisha Yakult Honsha; Ikeda, Takashi; Ono, Masahiro; Ueno, Satoshi; Yamazaki, Ryuta; Yaegashi, Takashi; Matsuzaki, Takeshi; US2014/343017; (2014); 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. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 90347-66-3

A mixture of 4 (7.26 g, 26.3 mmol), 11(3.0 g, 17.5 mmol), K2C03 (4.84 g, 35.0 mmol), DMEDA (386 mg, 4.38 mmol) and Cul (834 mg, 0.871 mmol) in 90 ml of dioxanewas stirred at 100 C under N2 for 18h. The mixture was filtered, concentrated and purified by column chromatography to give 12 (2.2 g, 39%) as a slightly yellow solid. LCMS (m/z: m+1): 320.2.

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; CARDIO THERAPEUTICS PTY LTD; TREUTLEIN, Herbert; ZENG, Jun; DIXON, Ian; JAMES, Ian; PALMER, James T; (169 pag.)WO2018/165718; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com