Category: iodides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 31599-60-7, name is 1-Iodo-2,3-dimethylbenzene, 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 31599-60-7, 31599-60-7

To a solution of 1-iodo-2,3- dimethylbenzene (8) [prepared according to Chen, Y et al. Org. Lett. 2007, 9, 1899] (1 .93 g, 8.32 mmol) in carbon tetrachloride (40 mL) was added NBS (3.67 g, 20.62 mmol), AIBN (0.070 g, 0.43 mmol) and the resulting mixture was gently refluxed by irradiation with a halogen lamp (500 W) for 4 h. The precipitate was filtered and washed with a small amount of carbon tetrachloride. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc ( 1 00 ml), successively washed with 10% NaOH solution (20 mL), water (2 x 20 ml), 10% Na2S203 solution (20 mL), water (20 mL), brine (20 raL), and dried (Na2SC>4). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether) to give 1 .89 g (58.3%) of compound 9. NMR (CDC13) delta: 7.84 (dd, J=8.1 , 1 .1 Hz, 1 H), 7.33 (dd, J=7.6, 1 .1 Hz, l H), 6.97 (t, J=7.8 Hz, 1 H), 4.85 (s, 2H), 4.66 (s, 2H). The product contained ca. 15-20% of an inseparable impurity (supposedly l -bromo-2,3-bis(bromomethyl)benzene).A mixture of 1,2-bis(bromomethyl)-3-iodobenzene (9) (2.50 g, 6.41 mmol), diethyl 2-acetamidomalonate (1 .39 g, 6.41 mmol), and K2C03 (2.22 g, 1 6.06 mmol) in acetonitrile (40 mL) was refluxed for 70 h. The mixture was allowed to cool to ambient temperature, the precipitate was filtered and washed with a small amount of acetonitrile. The filtrate was concentrated under reduce pressure, the obtained residue was dissolved in EtOAc (100 mL), washed successively with saturated NaHC03 solution (30 mL), water (2 x 30 mL), brine (30 mL), and dried (Na2S04). The solvent was evaporated and the residue was purified by column chromatography on silica gel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 2 g of oil. The oil was dissolved in diethyl ether and kept in a refrigerator overnight. The precipitate was filtered and dried to give 0.4 g (14%) of a regioisomer diethyl 2-acetyl-5-iodo-l ,4-dihydroisoquinoline-3,3(2H)-dicarboxylate. NMR (CDC13) delta: 7.76 (d, J=8.0 Hz, 1H), 7.13 (d, J=7.5 Hz, 1 H), 6.94 (t, J = 7.7 Hz, 1H), 4.65 (s, 2H), 4.19 (q, J=7.1 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 3.56 (s, 2H), 2.28 (s, 3H), 1 .22 (t, J=7.1 Hz, 3H), 1.22 (t, J=7.1 Hz, 3H). LCMS (ESI) m/z: 446 [M+H]+. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 20: 1 to 20:6) to give 0.95 g (33.2%) of compound (10).A solution of diethyl 2-acetyl-8-iodo-l,4-dihydroisoquinoline-3,3(2H)-dicarboxylate (10) (0.585 mmol) in 6 N HQ (10 mL) was refluxed for 5 h. The mixture was cooled and cone. NH4OH water solution was added until pH of the medium was ~7. The precipitate was filtered, washed with a small amount of water, and dried to give 0.305 g (76.7%) of compound (11). Because of a low solubility of the product in common deuterated organic solvents and deuterium oxide, the NMR spectrum was not informative. LCMS (ESI) m/z: 304 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid). LCMS (ESI) m/z: 256 [M+H]+.To a suspension of 8-iodo-l ,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (11) (0.645 g, 2.13 mmol) in methanol ( 1 8 mL) slowly SOCI2 ( 1.07 ml, 14.92 mmol) was added within 10 min. The reaction mixture was stirred at room temperature for 16 h, evaporated, and the residue was dissolved in a mixture of IN NaHC03 solution (30 mL) and EtOAc (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 ^ 15 mL). The organic extracts were combined, washed successively with water (20 mL), brine (20 mL), and dried (Na2S04). The solvents were evaporated to give compound 12 (0.570 g, 84%) which was used in the next step without further purification. NMR (CDCI3) delta: 7.67 (d, J=7.8 Hz, IH), 7.10 (d, J=7.5 Hz, I H), 6.87 (t, J=7.7 Hz, IH), 4.07 (d, 16.6 Hz, IH), 3.87 (d, J=16.6 Hz, I H), 3.78 (s, 3H), 3.71 (dd, J=9.4, 5.0 Hz, I H), 3.04 (dd, J=16.5, 5.0 Hz, IH), 2.97 (dd, J=l 6.5, 9.4 Hz, IH). LCMS (ESI) m/z: 318 [M+H]+. The product contained ca. 15-20% of an inseparable impurity (supposedly the corresponding bromo derivative methyl 8-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate). LCMS (ESI) m/z: 270 [M+H]+.A mixture of methyl 8-iodo-1, 2,3,4- tetrahydroisoquinoline-3-carboxylate (12) (0.570 g, 1 .8 mmol) and 2,3-dichloro-5,6-dicyano- 1 ,4-benzoquinone (DDQ) (0.449 g, 2.0 mmol) in toluene (20 mL) was refluxed for 6 h. To the reaction mixture was added another portion of DDQ (0.100 g, 0.45 mmol) and the refluxing was continued for 16 h. The mixture was allowed to cool to room temperature; the precipitate was filtered and washed with a small amount of toluene. The filtrate was evaporated and the residue was purified by column chromatography on silicagel (eluent petroleum ether-ethyl acetate, gradient from 100:0 to 100: …

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-Iodo-2,3-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; JIRGENSONS, Aigars; LOZA, Einars; CHARLTON, Michael; FINN, Paul William; RIBAS DE POUPLANA, Lluis; SAINT-LEGER, Adelaide; (76 pag.)WO2016/129983; (2016); 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 77317-55-6 as follows. 77317-55-6

Examples 13 to 21:; The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the type of the anthranilic acid derivative was changed. The results are shown in Table 4.

According to the analysis of related databases, 77317-55-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; EP1997812; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5471-81-8, 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 5471-81-8 as follows.

General procedure: To a 25mL of oven-dried Schlenk tube equipped with a magnetic stir bar was charged with [Pd(C3H5)Cl]2 (3.7mg 0.01mmol, 0.05 equiv), XPhos (10.5mg, 0.022mmol, 0.11 equiv), K2CO3 (69.1mg, 0.5mmol, 2.5 equiv), and dry CH3CN (1mL). After stirring for about 15minat r.t. under argon, a solution of aryl iodide 1 (0.24mmol, 1.2 equiv), alkylating reagent 2 (0.2mmol, 1.0 equiv), 5-Norbornene-2-carboxylic acid N4 (5.5mg, 0.04mmol, 0.2 equiv) in dry MeCN (1mL) was added, then heated to 70C and stirred for 5-24h. The reaction was monitored by TLC, after completion of the reaction, the mixture was cooled to r.t., filtered through a thin pad of celite eluting with ethyl acetate (10mL), and the combined filtrate was concentrated in vacuo. The residue was directly purified by column chromatography on silica gel or purified by PTLC to give the desired product 3.

According to the analysis of related databases, Methyl 4-iodo-3-methylbenzoate, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Ze-Shui; Qian, Guangyin; Gao, Qianwen; Wang, Peng; Cheng, Hong-Gang; Hua, Yu; Zhou, Qianghui; Tetrahedron; vol. 75; 12; (2019); p. 1774 – 1780;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 696-41-3, name is 3-Iodobenzaldehyde, molecular formula is C7H5IO, 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. 696-41-3.

General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiCl2.glyme (4.4mg, 0.02 mmol, 10 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrer bar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA(60 muL, 2 equiv.), N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) and H2O (7.2 muL, 2 equiv.) were subsequently added in this order. The mixture was then irradiated with blue LED (2 meter strip, 18 W)with ethylene balloon for 24 hours at 80oC (Figure S1). The reaction was added water (30 mL) and extracted with ethyl acetate (10 mL) three times. Combined organic layer was successively washed with brine three times and dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography (hexane or hexane/ethyl acetate) to yield theproduct

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

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 64248-58-4 name is 1,2-Difluoro-4-iodobenzene, 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. 64248-58-4

General procedure: A mixture of the corresponding carboxamide ((¡À)-1a-h or (¡À)-1iA or 1iB or 1j-(S)) (0.25 mmol), Pd(OAc)2 (2.8 mg, 5 mol %), aryl iodide (1.0 mmol, 4 equiv) and AgOAc (92 mg, 0.55 mmol, 2.2 equiv) in anhydrous toluene (3 mL) was heated at 110 C for 24-70 h (see the respective Tables/Schemes for the reaction time for the specific examples) under nitrogen atmosphere. After the reaction period, the reaction mixture was concentrated in vacuum and purification of the resulting reaction mixture by silica gel column chromatography furnished the corresponding beta-C-H arylated racemic compounds 3a-l, 4a-c, 5a, 6a-f, 8a-c, 8eA-hA, 8eB-hB and enantiomerically enriched 10a-c (see Tables/Schemes for the reaction conditions for the specific examples).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Difluoro-4-iodobenzene, and friends who are interested can also refer to it.

Reference:
Article; Gopalakrishnan, Bojan; Babu, Srinivasarao Arulananda; Padmavathi, Rayavarapu; Tetrahedron; vol. 71; 43; (2015); p. 8333 – 8349;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, Adding a certain compound to certain chemical reactions, such as: 624-75-9, name is 2-Iodoacetonitrile, 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 624-75-9.

General procedure: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

According to the analysis of related databases, 624-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

64248-58-4, A common compound: 64248-58-4, name is 1,2-Difluoro-4-iodobenzene, 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.

Example 40; 4- {6-[2-(3,4-Difluorophenyl)-l -ethynyl]-3-pyridazinyl}piperazino-2(trifluoromethyl)- phenylmethanone; Prepared by Sonogashira coupling reaction of Intermediate 6 with l,2-difluoro-4- iodobenzene in a mixture of triethylamine and DMSO to give the product as a white solid; IR (KBr) 2856, 2220, 1655, 1510, 1265, 1147, 1009 cm”1; 1H NMR (300 MHz, CDCl3) delta 3.32- 3.36 (m, 2H), 3.72-4.10 (m, 6H), 6.88 (d, J= 9.3 Hz, IH), 7.12-7.16 (m IH), 7.28-7.65 (m, 6H), 7.73 (d, J= 9.3 Hz, IH) ; ESI-MS (m/z) 472.62 (M)+.

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-Difluoro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; WO2008/62276; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

455-13-0, 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. 455-13-0 name is 4-Iodobenzotrifluoride, 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 25-mL flask was charged with Pd(OAc)2 (1.2 mg, 0.005 mmol), 1-iodo-4-nitrobenzene (1a, 127.0 mg, 0.5 mmol), K2CO3 (141.0 mg, 1.0 mmol), H2O (0.5 mL), and PEG 400 (2.0 mL); the flask was subjected to standard cycles (3 ¡Á) of evacuation and back-filling with dry and pure CO. The mixture was stirred at r.t. for the indicated time. The mixture was poured into sat. aq NaCl (15 mL), acidified to pH 3 with 3 M aq HCl, and extracted with EtOAc (3 ¡Á 15 mL). The solvent was removed from the combined organic phases on a rotary evaporator. The crude product was purified by column chromatography (silica gel, PE-EtOAc-HCO2H, 25:1:1) to afford 2a as a light yellow solid; yield: 75mg (90%); mp 238.0-239.3 C. 1H NMR (400 MHz, DMSO-d6): delta = 13.68 (br s, 1 H), 8.30 (d, J = 8.0 Hz,2 H), 8.14 (d, J = 8.0 Hz, 2 H). 13C NMR (100 MHz, DMSO-d6): delta = 165.9, 150.0, 136.4, 130.7, 123.8.

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

Reference:
Article; Han, Wei; Jin, Fengli; Zhou, Qing; Synthesis; vol. 47; 13; (2015); p. 1861 – 1868;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

135050-44-1, A common compound: 135050-44-1, name is 3-Chloro-4-iodoaniline, 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.

2-Ethynylpyridine (0.57 mL, 5.6 mmol), 4-iodo-3-chloroaniline (1.01 g, 4.0 mmol), PdCl2(PPh3)2 (281 mg, 0.4 mmol), copper (I) iodide (152 mg, 0.8 mmol), trimethylamine (5.6 mL, 40 mmol) and DMF (4.5 mL) were added to a vial with a stirbar and the mixture was sparged with Argon. The reaction mixture was heated in a 90 C heating block for 45 min then cooled to ambient temperature. The mixture was partitioned between water and ethyl acetate, and the organic layer was washed with brine, dried over Na2S04, filtered and evaporated under reduced pressure. The crude product was purified by gradient flash column chromatography from 0 – 100% EtOAc in hexanes to yield 660 mg (72%) of 3-chloro-4-(pyridin-2-ylethynyl)aniline (12) as a yellow solid. 1H MR (400 MHz, CDC13) delta 8.61 (s, 1H), 7.69 (t, J= 7.7 Hz, 1H), 7.54 (d, J= 7.8 Hz, 1H), 7.41 (d, J= 8.4 Hz, 1H), 7.26 – 7.21 (m, 1H), 6.72 (s, 1H), 6.53 (d, J= 8.4 Hz, 1H), 3.95 (br s, 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, 3-Chloro-4-iodoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH; UNIVERSITAeT BREMEN; PETRASSI, Hank Michael James; PERAM SURAKATTULA, Murali Mohan Reddy; MAEDLER, Kathrin; ARDESTANI, Amin; ROLAND, Jason T.; BAGULEY, Tyler D.; TREMBLAY, Matthew S.; SHEN, Weijun; SCHULTZ, Peter G.; CHATTERJEE, Arnab K.; (155 pag.)WO2016/210345; (2016); 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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, A new synthetic method of this compound is introduced below., 3032-81-3

1,3-Dichloro-5-iodobenzene (2.73 g, 10 mmol) was added to the reaction flask under an argon atmosphere.3,5-dichlorothiophenol (2.15 g, 12 mmol), cuprous iodide (9.5 mg, 0.5 mmol),Potassium carbonate (6.9 g, 50 mmol) and 50 ml of DMF solvent were stirred and heated to 120 ¡ã C for 12 h.After the reaction was stopped, the solvent was evaporated to dryness and extracted with dichloromethane.Purified by silica gel column chromatography, petroleum ether / dichloromethane mixed solvent (15 / 1, v / v) as a rinse to give a white solid, yield 75percent;

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; South China Xietong Chuangxin Institute; Ying Lei; Hu Liwen; Huang Fei; Cao Yong; (25 pag.)CN109096159; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com