Category: iodides-buliding-blocks

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. 25245-29-8, name is 5-Iodo-1,2,3-trimethoxybenzene, A new synthetic method of this compound is introduced below., Computed Properties of C9H11IO3

Step 1: 2-(3,4,5-Trimethoxy-phenyl)-2,3-dihydro-furan (287) To a solution of 5-iodo-1,2,3-trimethoxybenzene (900 mg, 3.06 mmol) and 2,3-dihydrofuran (1.16 mL, 15.3 mmol) in dry DMF (8 mL) were added PPh3 (20 mg, 0.077 mmol), KOAc (901 mg, 9.18 mmol), n-Bu4NCl (850 mg, 3.06 mmol) and Pd(OAc)2 (17 mg, 0.077 mmol). The reaction mixture was stirred 18 h at 80 C. The reaction mixture was diluted with AcOEt and water. After separation, the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/Hexane: 20/80) to afford the title compound 287 (311 mg, 1.32 mmol, 43% yield). 1H NMR: (300 MHz, CDCl3) delta (ppm): 6.59 (s, 2H), 6.45 (m, 1H), 5.45 (dd, J=10.5, 8.4 Hz, 1H), 4.97 (m, 1H), 3.87 (s, 6H), 3.84 (s, 3H), 3.06 (m, 1H), 2.62 (m, 1H).

The synthetic route of 25245-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MethylGene, Inc.; US2004/142953; (2004); A1;; ; Patent; MethylGene, Inc.; US6897220; (2005); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 31599-60-7, name is 1-Iodo-2,3-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. Computed Properties of C8H9I

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]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 31599-60-7, its application will become more common.

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 173406-17-2 as follows. Recommanded Product: 173406-17-2

To a mixture of 244 mg of 3- (2-aminoetliyl) pyridine (2.0 mmol) and 604 mg of t-butyl 3- iodobenzoate (2.0 mmol) in 10 [ML] of toluene was added 250 mg of sodium t-butoxid (2.5 [MMOL),] 30 mg [OF TRI-T-BUTYLPHOSPLIONIMN TETAFLUOROBORATE] (0.1 mmol) and 50 mg of tris (dibenzylidineacetone) dipalladium [(0)] (0.055 [MMOL).] The mixture was stirred for 16 h and filtered through celite. The celite was washed with 3 X 5 mL of toluene and the filtrate was concentrated in vacuo. The residue was purified by column [CHROMATOGRAPHY] using 35%-45% EtOAc in hexanes as eluant to give 103 mg of t-butyl N- (2- (3-pyridyl) ethyl)-3-aminobenzoate as a bright yellow oil (17% yield).

According to the analysis of related databases, 173406-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2004/9552; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 19094-56-5, 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.

1. Synthetic routeWherein, the condition (b) is (COCl)2, CH2Cl2, DMF/Pyr, CH3OH, 2 to 3 h, r.t.2, the synthesis step(1) The compound B (B1,B2,B3) of the compound of Example 1 after purification (1 g, 3.16 mmol, 3.16 mmol, 3.54 mmol) was weighed under nitrogen, after adding 20 mL of ultra-dry anhydrous dichloromethane (DCM) and stirring to dissolve completely, add three times the amount of oxalyl chloride (9.48 mmol, 9.48 mmol, 10.62 mmol) and stir for 20-30 min; (2) Under nitrogen protection, 0.1 mL of anhydrous grade N,N-dimethylformamide (DMF) was added. After reacting for 1 h at room temperature, The reaction activated product is vacuum dried, And minimize external air entering the reaction device during operation; Use nitrogen as a shielding gas and add ultra-dry dichloromethane solvent. After stirring and dissolved at room temperature, Add twice the amount of anhydrous pyridine (6.32 mmol, 6.32 mmol, 7.08 mmol), The reaction was stirred for 30 min; finally, twice the amount of ultra-dry methanol (6.32 mmol, 6.32 mmol, 7.08 mmol) was added under a nitrogen atmosphere at room temperature. The reaction was stirred for 3 h or more; the reaction end point was detected by TLC [developing agent: V (petroleum ether)/V (ethyl acetate) = 20/1];(3) After the reaction is completed, it is extracted by washing with ethyl acetate. And dried over anhydrous MgSO4, filtered and concentrated. The crude product of the intermediate C(C1,C2,C3) was obtained, purified by silica gel column chromatography [eluent: V ( petroleum ether) / V (ethyl acetate) = 50/1] obtaining the compound intermediate C (C1,C2,C3), colorless oily liquid with yields of 72%, 58% and 63%, respectively.

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; Guangdong University of Technology; Zhao Suqing; Zhang Bingjie; Feng Dongyan; Zhong Yingying; Huang Jinqu; Wu Ke; Ling Huaying; Tan Qiting; Chen Yanting; Zhao Jiawei; Ma Zhuolin; Jiang Zhengyun; Yang Yang; Zhu Qiuyan; Hong Weiqian; (37 pag.)CN110143869; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 450412-29-0, A common heterocyclic compound, 450412-29-0, name is 1-Bromo-3-fluoro-2-iodobenzene, molecular formula is C6H3BrFI, 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.

28.3 g (100 mmol, 1.0 eq.) m-bromoiodobenzene and 25.8 g m-bromoaniline (150 mmol, 1.5 eq.)It was placed in a dry 3 L three-necked flask, and then dried and degassed 1100 ml of toluene was added as a solvent.Nitrogen gas was passed for 15 minutes. Add 2.9g (15% mol) of cuprous iodide,5.9 g (30% mol) of 1,10-phenanthroline and 63.7 g (300 mol, 3 eq.) potassium phosphate.The temperature was raised to 110 C and the reaction was carried out for 18 hours. After the reaction is completed, cool to room temperature, suction filtration,Rotating to remove the solvent,Recrystallization with toluene and ethanol,27.8 g of intermediate L were obtained,The yield was 85%.

The synthetic route of 450412-29-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Jin Zhenyu; Qian Chao; Wang Xiaowei; Dai Peipei; (49 pag.)CN108164511; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 35453-19-1, A common heterocyclic compound, 35453-19-1, name is 5-Amino-2,4,6-triiodoisophthalic acid, molecular formula is C8H4I3NO4, 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.

5-Amino-2,4,6-triiodoisophathalic acid (15.38 g, 27.5 mmol, 1.0 equiv.) was refluxed in SOCl2 ( 10OmL, 1.37 mol, 50.0 equiv.) for 4 hours. The volatiles were removed in vacuo and the resultant dark yellow residue was dissolved in ethyl acetate (300 mL). The organic layer was washed with sat. NaHCO3 (3 x 150 mL), water (3 x 150 mL) and brine (150 mL) and concentrated in vacuo. The residue was dissolve in toluene and passed through a short pad of silica, dried (MgSO4) and concentrated in vacuo to yield the title compound as a beige solid (10.74 g, 66 %). IR spectrum in KBr disc/cm”1: v(N-H) 3370, 3470; V(C=O) 1770, 1798

The synthetic route of 35453-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; KINGS COLLEGE LONDON; GUYS AND ST THOMAS NHS FOUNDATION TRUST; WO2007/26140; (2007); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference 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.

The above white powder compound (10 g, 14.2 mmol) was dissolved in 20 mL of DMAcIn a mixture with acetonitrile (1:1), the temperature is lowered to 10 C, and the temperature is controlled below 30 C.Dropping (the purpose of dropping is controlled to a temperature not exceeding 30 C) Chloroacetyl chloride(9.65g, 92.3mmol), after the addition was completed, the temperature was raised to 50 C, and after stirring for 3 hours,Cool to 15 C, drop (the purpose of the drop control temperature does not exceed 25 C)20mL 10mol / L NaOH aqueous solution, stirring reaction at 25 C for 1 h,After the reaction was completed, the pH was adjusted to 4 with dilute hydrochloric acid, and the mixture was allowed to stand overnight at 0 C, and filtered.The filter cake is washed several times with water and dried (dried to sample to 85 C).GotN,N-(2′,3′)-Dihydroxypropyl-3,5-dimethylformamide-(2,4,6-)beta-amino group.

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; China Calculate University; Wu Zhiping; Bai Xueyan; Wu Yuqi; (13 pag.)CN108727376; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 51628-12-7, The chemical industry reduces the impact on the environment during synthesis 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, I believe this compound will play a more active role in future production and life.

General procedure: Cooling at 0 C, a solution of 4-substituted- or 3,4-disubstituted-phenylacetonitrile or of cyanolupinane42 (6 mmol) and 0.35 mL of abs. EtOH in 5 mL of CHCl3 was saturated with anhydrous HCl and left overnight at 0-5 C.

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-(4-Iodophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tonelli, Michele; Novelli, Federica; Tasso, Bruno; Vazzana, Iana; Sparatore, Anna; Boido, Vito; Sparatore, Fabio; La Colla, Paolo; Sanna, Giuseppina; Giliberti, Gabriele; Busonera, Bernardetta; Farci, Pamela; Ibba, Cristina; Loddo, Roberta; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4893 – 4909;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 35944-64-0,Some common heterocyclic compound, 35944-64-0, name is 3-Iodo-4-methylaniline, molecular formula is C7H8IN, 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.

Reference Example 4 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)aniline (Compound A4) 3-Iodo-4-methylaniline (1.97 g, 8.45 mmol) and bis(pinacolate)diboron (2.32 g, 9.13 mmol) were dissolved in DMSO(23 mL), and potassium acetate (2.87 g, 29.2 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (345 mg, 0.423 mmol) were added thereto, followed by stirring at 80C for 4 hours under argon atmosphere. To the reaction mixture were added ethyl acetate and water, and insoluble materials were filtrated off through celite, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, followed by drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by si lica gel column chromatography (ethyl acetate/hexane = 6/1) to obtain Compound A4(1.36 g, 69%). 1H NMR (300 MHz, CDCl3) delta (ppm) 1.33 (s, 12H), 2.42 (s, 3H), 3.51 (br s, 2H), 6.68 (dd, J = 8.1, 2.7 Hz, 1H), 6.97 (d, J = 8.1 Hz, 1H), 7.11 (d, J = 2.7 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Iodo-4-methylaniline, its application will become more common.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2269993; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 16932-44-8, name is 2-Iodo-1,3-dimethoxybenzene, 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 16932-44-8, Recommanded Product: 2-Iodo-1,3-dimethoxybenzene

General procedure: To a stirred solution of aryl halide (1.2mmol) and [Pd(pp3S4)(dba)] (1mol %) in isopropanol (2.5ml) was added nitrogen/oxygen nucleophile (1mmol) followed by Cs2CO3 (2mol %) in the atmosphere of air. The mixture was heated to 80C and the progress of the reaction was monitored by TLC. After completion, the solvent was evaporated through rotavapour and the crude mixture was washed with dichloromethane-H2O and the organic phase was separated and dried over Na2SO4. The dichloromethane was evaporated followed by flash column purification on silica gel of the crude to obtain the pure products. The products were characterized using 1H, 13C NMR spectroscopy and GC-MS spectroscopy. The characterization data were in good agreement with those described in the literature.

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-Iodo-1,3-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Majumder, Arpi; Gupta, Ragini; Mandal, Mrinmay; Babu, Madhu; Chakraborty, Debashis; Journal of Organometallic Chemistry; vol. 781; (2015); p. 23 – 34;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com