Category: iodides-buliding-blocks

135050-44-1, The chemical industry reduces the impact on the environment during synthesis 135050-44-1, name is 3-Chloro-4-iodoaniline, I believe this compound will play a more active role in future production and life.

Example 55: N-(5-Chloro-2-( (E)-3-f3-( 4-fluoro-benzvl)-3,8-diaza-bicvclof3.2.110ct-8-vll-3-oxo- propenyl(at)-4-pyrazin-2-yl-phenyl)-acetamide; a) 3-Chloro-4-pvrazin-2-vl-phenylamine; 3-Chloro-4-iodo aniline (0. 349 g; 1.375 mmol ), 2- (tri-n-butylstannyl)pyrazine and (1.015 g; 2.75 mmol) PdC12(PPh3)2 (0.193 g; 0.16 mmol) are dissolved in xylene (5 ml) and refluxed for 2.5 h. The reaction mixture is taken up in TBME and extracted with 2N HCI three times. The combined HC-phases are poured on a saturated solution of saturated Na2C03 and extracted with TBME three times. The combined organic phases are dried over Na2S04, filtered and evaporated to dryness and purified via chromatography (Si02, acetone/hexanes 1/3) to yield the desired product as yellow crystals (162 mg; 57 %). 1 H-NMR (400MHz; DMSO-d6), No. (ppm) : 5.78 (s, 2H) ; 6.62 (dd, 1 H); 6.70 (d, 1H) ; 7.34 (d, 1H) ; 8.50 (d, 1 H); 8.63 (m, 1 H); 9.48 (s, 1 H). MS (m/z) ES+: 206 (MH+).

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-4-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/103054; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 19094-48-5, name is 3,5-Diiodobenzoic acid, molecular formula is C7H4I2O2, 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. 19094-48-5

S3.ll: To a solution of S3.10 (6.8 g, 18 mmol) in methanol (200 mL) was added sulfuric acid (0.5 mL). The reaction mixture was refluxed for 7.5 hours, then after cooling concentrated and deionized water (200 mL) was added. A dark-brown solid was collected by filtration and purified by column chromatography (silica gel; hexanes:ethyl acetate = 8:2). The product was obtained as a white powder, 4.2 g (59.2%), by recrystallization from methanol/water. NMR (300 MHz, CDC13): delta 8.29 (d, J= 1.6 Hz, 2H), 8.20 (t, J= 1.6 Hz, 1H), 3.90 (s, 13 delta 163.97, 148.99, 137.56, 133.08, 94.32, 52.73.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19094-48-5, its application will become more common.

Reference:
Patent; GEORGIA TECH RESEARCH CORPORATION; ZUNIGA, Carlos; MARDER, Seth; HASKE, Wojciech; KIPPELEN, Bernard; FENG, Daijun; WO2014/11491; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

610-97-9, 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. 610-97-9 name is Methyl 2-iodobenzoate, 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.

Methyl 2-iodobenzoate (25 g, 95 mmol), prop-2-yn-1-ol (8.02 g, 143 mmol) and TEA (26.6 ml, 191 mmol) were added to a deareated mixture of Pd(PPh3)4 (0.220 g, 0.191 mmol), copper(I) iodide (0.073 g, 0.382 mmol) in DMF (60 ml). The resulting mixture was stirred at 90C for 5 hrs and then at 40C overnight. The reaction mixture was poured into EtOAc (600 ml) and washed with brine (600 ml). Organic phase wasthen concentrated and the dark oil was rinsed with Et20 (600 ml). The mixture was filtered, and then concentrated to give the title compound as deeply brown oil (13.0 g). This compound was used in the next step without any further purification and characterization.UPLC-MS: 1.53 mi [M+H-18]+. (Method 4)

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

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; CAPELLI, Anna Maria; ACCETTA, Alessandro; CARZANIGA, Laura; WO2015/91685; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 71838-16-9, 71838-16-9

The cadmium reagent was generated as in Example 1 using Cd metal (8.5 g, 0.075 mole), diethyl bromodifluoromethylphosphonate (18 g, 0.068 mole) and AcOH (1.0 niL) in DMF (80 mL). A 40 mL aliquot of this solution was added to CuCl (6.72 g, 0.068 mole) followed after 2 minutes by the addition of 3-bromo-4-iodotoluene (5.0 g, 0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with additional ether (300 mL) and the combined ether layer was washed with saturated ammonium chloride (500 mL) and water (500 mL) then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/ hexanes afforded 4.4 g of (2-bromo-4-methyl-phenyl)difluoromethylphosphonic acid diethyl ester. To the diethyl ester material obtained, (1.8 g, 0.005 mole) in carbon tetrachloride (CCl4, 30 mL), were added AIBN (0.033 g, 0.0002 mole) and N- bromosuccinimide (NBS, 0.89 g, 0.005 mole). The reaction was heated at reflux for 2 hours (a thin white suspension formed). The reaction was allowed to reach room temperature and the solvent was removed under vacuum. The residue was taken up in ethyl acetate (EtOAc, 120 mL) and washed with saturated NaHCtheta3 (60 mL) and brine (60 mL) then dried over MgSO4. Filtration and solvent evaporation afforded 2.1 g of crude product. Flash chromatography on silica gel using 20-30% ethyl acetate/hexanes afforded 1.11 g of (2- bromo-4-bromomethyl-phenyl)-difluoro-methylphosphonic acid diethyl ester.; Example 25 – Synthesis of Compound 25(2-Bromo-4-methylphenyl) difluoromethylphosphonic acid diethyl ester 25 To a suspension of 8.5 g Cd metal (0.075 mole), in 80 mL DMF (dried over 4A molecular sieves for 24 hours) was added 18 g of diethyl bromodifluoro-methylphosphonate (0.068 mole) and 1 mL glacial acetic acid. Within 4 minutes an exotherm started and lasted EPO ? for 20 minutes. The suspension was stirred for 3 hours and allowed to stand at room temperature for 30-40 minutes. A 40 mL aliquot of this solution was added to 6.72 g of CuCl (0.068 mole) followed after 2 minutes by the addition of 5 g of 3-bromo-4-iodotoluene (0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with 300 mL of ether and the combined ether layer was washed with 500 mL of saturated ammonium chloride and 500 mL of water, then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/hexanes afforded 4.4 g of Compound 25.

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-Bromo-1-iodo-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEPTYR, INC.; WO2006/55525; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

696-41-3, name is 3-Iodobenzaldehyde, 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. 696-41-3

To a mixture of compound 1 (326 mg, 2.5 mmol), compound 214 (582 mg, 2.5 mmol), and PdCl2(PPh3)2 (37 mg, 0.05 mmol) in a flame-dried Schlenk tube were added THF (15 mL) and Et3N (5 mL) under argon atmosphere and followed by the addition of CuI (10 mg, 0.05 mmol) 10 min later. The mixture was stirred at room temperature for 9 h and then water (20 mL) and brine (20 mL) were added. After being extracted with ethyl acetate (3¡Á30 mL), the combined organic phase was washed with brine and dried over sodium sulfate. Upon removal of the solvent under reduced pressure, the resulting residue was purified by column chromatography (petroleum ether/dichloromethane 1:1) to give compound 3 as a pale yellow solid (487 mg, 83%). Mp 77-78 C. 1H NMR (300 MHz, CDCl3): delta 7.49 (t, J=7.2 Hz, 1H), 7.54-7.64 (m, 2H), 7.67 (d, J=7.5 Hz, 1H), 7.81 (d, J=7.5 Hz, 1H), 7.90 (d, J=7.5 Hz, 1H), 7.96 (d, J=7.5 Hz, 1H), 8.07 (s, 1H), 10.03 (s, 1H), 10.63 (s, 1H). 13C NMR (100 MHz, CDCl3): delta 86.4, 94.5, 123.6, 126.0, 127.6, 129.1, 129.3, 129.7, 132.9, 133.4, 133.9, 135.9, 136.6, 137.1, 191.3, 191.3. MS (EI): m/z 234 [M]+. HRMS (EI): calcd for C16H10O2 [M]+: 234.0681, found 234.0687. IR (KBr, cm-1): 3064, 2834, 2732, 2208, 1703, 1591, 1284, 1200.

Statistics shows that 696-41-3 is playing an increasingly important role. we look forward to future research findings about 3-Iodobenzaldehyde.

Reference:
Article; Wang, Liu-Gang; Zhan, Tian-Guang; Zhao, Xin; Jiang, Xi-Kui; Li, Zhan-Ting; Tetrahedron; vol. 68; 26; (2012); p. 5303 – 5310;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

112671-42-8, 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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows.

9.9-dimethyl acridine (10 g, 47.8 mmol) under nitrogen4-bromo-1-iodo-2-nitrobenzene (32.74 g, 99.85 mmol),Potassium carbonate (13.8 g, 99.85 mmol), copper (6.35 g, 99.85 mmol),Ethylene glycol (350 ml) was stirred, and the reaction was stirred at about 100 C for about 1 hour.It was extracted with acetone, and the organic layer was taken, and a hydrochloric acid solution (hydrochloric acid: deionized water = 1:10 vol.%) (500 ml) was added.After washing with deionized water,Recrystallization of acetone and methanol,Intermediate 1-1 (12 g, 59%) was obtained.

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; Jilin Aolaide Optoelectric Materials Co., Ltd.; Jin Furong; He Jinxin; Wang Shikai; (16 pag.)CN108727374; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, molecular formula is C6H3F2I, 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. 64248-58-4.

General procedure: A vial was charged with 2-Hydroxy-4-methoxybenzaldehyde (1.97 mmol, 300 mg), PdCl2 (5 mol%, 17.5 mg), 1,2-Difluoro-4-iodobenzene (2 equiv., 946.7 mg), Na2CO3 (2 equiv., 418.1 mg), LiCl (0.4 equiv., 16.7 mg), and DMF (19.7 mL, 0.1 M of the aldehyde), purged with N2 and stirred at 110 C 4-10 h. The reaction was monitored with LC-MS and TLC (TLC conditions: Aliquot was diluted with CH3OH, eluted with EtOAc/heptane 1:3, and stained with 2,4- dinitrophenylhydrazine solution). The reaction mixture was filtered over a pad of Celite, diluted with EtOAc, washed 3 times with water, and the aqueous layers was acidified and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4, concentrated and purified on silica using EtOAc/Heptane 1:20 ? 1:9 step gradient) to afford 2′-hydroxybenzophenone in 69.3% yield. (NMR data is given in the supporting information).

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

Reference:
Article; Saleeb, Michael; Mojica, Sergio; Eriksson, Anna U.; Andersson, C. David; Gylfe, Asa; Elofsson, Mikael; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1077 – 1089;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 82998-57-0, name is 3-Iodo-4-methylbenzoic acid, molecular formula is C8H7IO2, 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. 82998-57-0

To a solution of 3-iodo-4-methyl-benzoic acid (10.0 g, 38.2 mmol) in methanol (70 ml) is added concentrated sulfuric acid (0.5 ml). The reaction mixture is heated at 70 C. for 48 hours, cooled to room ambient temperature and then concentrated. After that, ethyl acetate (100 ml) and aqueous NaHCO3 (saturated, 100 ml) solution are added to the residue. The organic layer is separated and washed again with aqueous NaHCO3 (saturated, 100 ml) solution. The organic layer is separated, dried over anhydrous Na2SO4 and concentrated to yield 3-iodo-4-methyl-benzoic acid methyl ester 1. It is used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) delta 8.31 (s, 1H), 7.87 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=8.4 Hz), 3.85 (s, 3H), 3.35 (s, 3H); LC-MS m/z: 277.0 (M+1).

The chemical industry reduces the impact on the environment during synthesis 3-Iodo-4-methylbenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; IRM LLC; US2009/203666; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

124700-41-0, The chemical industry reduces the impact on the environment during synthesis 124700-41-0, name is 2-Fluoro-5-iodobenzoic acid, I believe this compound will play a more active role in future production and life.

Add bis (triphenylphosphine) palladium (II) dichloride (70 mg, 0. 10 mmol), copper (I) iodide (38 mg, 0. 20 mmol), and 3-ethynyl-5-methoxypyridine, (prepared as described in PREPARATION 10), (400 mg, 3. 0 mmol) to a solution of 2-fluoro-5-iodobenzoic acid (0. 53 g, 2. 0 mmol) in triethylamine (4. 2 mL, 30. 0 mmol) and stir at room temperature for 1 h. Heat at 50 C for 18 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 100 : 0 to 60 : 40 ethyl acetate : methanol. Triturate the resulting solid with 3 : 1 hexanes : methanol to give the title compound as an off-white solid (295 mg, 54%). 1H NMR (300 MHz, DMSO-d6) 6 3. 86 (s, 3H), 7. 09-7. 17 (m, 1H), 7. 46-7. 53 (m, 1H), 7. 55-7. 59 (m, 1H), 7. 81-7. 87 (m, 1H), 8. 24-8. 35 (m, 2H) ; MS (APCI) : m/z = 272 [M+H] +.

The chemical industry reduces the impact on the environment during synthesis 2-Fluoro-5-iodobenzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

608-28-6, 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. 608-28-6 name is 2-Iodo-1,3-dimethylbenzene, 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.

General procedure: A 10-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirring bar was flame-dried under vacuum and filled with argon after cooling to room temperature. To this tube were added 2-substituted 2H-indazole (1: 0.40 mmol), CuI (7.6 mg, 0.04 mmol), 1,10-phenanthroline (7.2 mg, 0.04 mmol), LiOt-Bu (64 mg, 0.80 mmol), and haloarene (2: 0.80 mmol), followed by DMF (0.5 mL) under a stream of argon. The tube was sealed with O-ring tap, and then heated at 110 C for 15 h in an eight-well reaction block with stirring. After cooling the reaction mixture to room temperature, the mixture was passed through a short pad of Celite (EtOAc). The filtrate was concentrated and the residue was subjected to preparative HPLC (acetonitrile/water as an eluent) to afford the arylated product 3.

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:
Conference Paper; Hattori, Keika; Yamaguchi, Kazuya; Yamaguchi, Junichiro; Itami, Kenichiro; Tetrahedron; vol. 68; 37; (2012); p. 7605 – 7612;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com