Month: May 2021

Reference of 696-41-3, 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. 696-41-3, name is 3-Iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1) 1-(3-Iodo-phenyl)-pent-4-en-1-ol To a stirred solution of 3-iodo-benzaldehyde (3.0 g, 12.93 mmol) in dry THF (45 mL) at -78 C. under nitrogen was added 0.5 M 3-butenyl magnesium bromide in THF (25.86 mL, 12.93 mmol) over 20 min. The reaction was stirred for 0.5 h and allowed to warm to -30 C. over 1 h and then quenched with sat ammonium chloride (20 mL). The reaction was diluted with water (10 mL) and then extracted with ethyl acetate (2*50 mL). The extracts were dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (5% to 10% ethyl acetate/petroleum ether) gave the title compound as a clear oil (3.5 g, 95%) and was used directly in the next step.

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

Reference:
Patent; WYETH; US2009/48320; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 16355-92-3,Some common heterocyclic compound, 16355-92-3, name is 1,10-Diiododecane, molecular formula is C10H20I2, 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.

Example 9 (n=10); (a) 1, 1′-[(Decane-1,10-diyl)dioxy]bis[(11S,11aS)-10-(tert- butylOxyCarbonyl)-8-methoxy-11-(tetrahydro-pyran-2-ylOxy)- 1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5- one] (8h); 1,10-Diiododecane (87.8 mg, 0.22 mmol, 0.5 equiv) was added to the mixture of monomer 7 (0.2 g, 0.44 mmol, 1.0 equiv) and potassium carbonate (0.98 mmol, 2.2 equiv) in dry DMF (30 mL), and the resulting mixture was heated to 90C under a nitrogen atmosphere for 5 h. Removal of excess solvent under reduced pressure afforded a crude solid, which was subjected to flash column chromatography (Si02, 50% EtOAc-hexane) to afford the dimerized compound 8h (191 mg, 0.1 8mmol, 82% yield, mixture of diastereomers from THP protecting group) as a solid: [a] 20D = +75 (c = 0.10, CHCl3); 1H NMR (CDCl3, 400 MHz): 5 1.25-1. 59 (m, 76H, 14-H, 15-H, 16-H, Boc, THP), 1. 68-1. 92 (16H, 13-H, THP), 1. 93-2. 20 (m, 16H, 1-H, 2-H), 3.45- 3.75 (m, 16H, 3-H, lla-H, THP), 3.83-4. 14 (m, 24H, 12-H, 7-OMe, THP), 5.02-5. 10 (m, 2H, THP), 5.12-5. 19 (m, 2H, THP), 5.69-5. 77 (d, 2H, 11-H), 5.79-5. 89 (d, 2H, 11-H), 6.49 (s, 2H, 9-H), 6. 86 (s, 2H, 9-H), 7.17 (s, 2H, 6-H), 7.21 (s, 2H, 6-H) ; 13C NMR (CDCl3, 400 MHz): 5 19. 9, 20.4, 23.1, 23.2, 25.2, 25.3, 25.9, 28.1, 28.2, 28. 9,29. 0,29. 1,29. 2,29. 3,29. 5,30. 9,31. 3,46. 3, 55. 9, 56. 2, 60. 0,60. 1, 63.3, 69. 1, 80.9, 81.2, 88.2, 91.2, 95. 8, 100. 2, 111.1, 111.5, 113.4, 114.0, 121.6, 126. 4,141. 0,143. 1,148. 1, 148.4, 155.4, 167.4, 167.6 ; IR (neat): 2937,1703, 1643, 1604, 1513,1450, 1392,1327, 1218,1164, 1022cm~1 ; MS (FAB) m/z (relative intensity) 1057 ( [M + Na] +’, 34), 1035 (M+., 100), 833 (26), 933 (25).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,10-Diiododecane, its application will become more common.

Reference:
Patent; SPIROGEN LIMITED; WO2005/85259; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 620621-48-9, 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. 620621-48-9, name is Methyl 2-chloro-5-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 77 :methyl 2-chloro-5-(3-(diethylamino)pyrrolidin-l-yl)benzoate; Methyl 2-chloro-5-iodobenzoate (1.00 g, 3.37 mmol), cesium carbonate (1.648 g, 5.06 mmol), BINAP (0.105 g, 0.17 mmol), palladium(II) acetate (0.038 g, 0.17 mmol) and 7V,7V-diethylpyrrolidin-3 -amine (0.576 g, 4.05 mmol) were suspended in dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 120 0C for 2 hours in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite before concentrating in vacuo. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% NH3ZMeOH in DCM. The product was isolated but still contained less polar impurities. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3ZMeOH and pure fractions were evaporated to dryness to afford methyl 2- chloro-5-(3-(diethylamino)pyrrolidin-l-yl)benzoate (0.257 g, 24.52 %) as a brown gum. mZz (ESI+) (M+H)+ =311; HPLC tR = 1.16 min. 1H NMR (400.13 MHz, DMSO-d6) delta 0.96 (6H, t), 1.80 – 1.85 (IH, m), 2.11 – 2.17 (IH, m), 2.54 – 2.63 (4H, m), 2.99 (IH, t), 3.15 – 3.22 (2H, m), 3.40 – 3.44 (2H, m), 6.53 – 6.56 (2H, m), 7.16 – 7.18 (IH, m), 7.42 (IH, s), 7.67 (IH, s).

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

Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/47558; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1829-28-3, 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. 1829-28-3, name is Ethyl 2-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: NaOtBu (98percent purity, 353 mg, 3.6 mmol) was dried by a vacuum pump for 30 min at room temperature. To a solution of NaOtBu in THF (3 mL) was added DIBAL-H (1.04 M, 3.27 mL, 3.4 mmol) at 0 °C under argon atmosphere and the obtained mixture was stirred for 1 h at room temperature. Then, ethyl benzoate (150.06 mg, 2.0 mmol) in THF (4 mL) was added to the solution at 0 °C, and the obtained mixture was stirred for 4 h. Finally, aq NH3 (concentration: 28.0percent-30.0percent, 4 mL) and I2 (2.08 g, 4.1 equiv) were added at 0 °C, and the obtained mixture was stirred for 3 h at room temperature. Then the reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL.x.3). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent under reduced pressure, the residue was treated with flash short column chromatography on silica gel (eluent: hexane/ethyl acetate=9:1) to afford benzonitrile (156.7 mg, 76percent yield)

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, Ethyl 2-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Suzuki, Yusuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 67; 41; (2011); p. 7956 – 7962;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference 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 4General Procedure for the Preparation of Alkyl Ester IodidesAlkyl ester iodides were prepared via reaction between methyl 2-methylpropanoate and appropriate alkyl diodide in the presence of butylithium and diisopropylamine according to the following process: under inert atmosphere, N,N-diisopropylamine (1.1eq) was dissolved in tetrahydrofuran (10eq). To the solution cooled down to 0 C. was added n-butyllithium (1.1eq) drop by drop. The solution was then cooled to -70 C. before adding 2-methylpropanoic acid (1eq). The mixture was stirred at -70 C. for 15 minutes. The appropriate diiodated derivative (2eq) was added drop by drop at -70 C., and then the reaction mixture was gradually warmed to room temperature and stirred for 20 hours. The solution was then hydrolysed by adding HCl 2N to reach acidic pH. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was chromatographed over silica gel.Example 4.1 methyl 2,2-dimethyl-5-iodo-pentanoate Prepared following the general procedure previously described using methyl 2-methylpropanoate and 1,3-diiodopropane. The residue was chromatographed over silica gel (eluent cyclohexane). The product was obtained as a pale yellow oil. Yield: 79% Rf (cyclohexane/ethyl acetate 98/2): 0.32 NMR 1H (CDCl3): 1.20 (s, 6H); 1.62 (m, 2H); 1.78 (m, 2H); 3.15 (t, 2H, J=7 Hz); 3.69 (s, 2H).

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; GENFIT; US2010/4159; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, 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 19094-56-5, HPLC of Formula: C7H4ClIO2

General procedure: To a solution of the appropriate carboxylic acid (1.88 mmol) in anhydrous DMF (4 mL) were successively added, N,N’-dicyclohexylcarbodiimide (427 mg, 2.07 mmol) and 1-hydroxybenzotriazolehydrate (280 mg, 2.07 mmol) under argon. The reaction was stirred at room temperature for 30 min, and a solution of N,N-diethylethylenediamine (291 mL, 2.07 mmol) in distilled N,N-diisopropylethylamine (655 mL, 3.76 mmol) was added. The resulting mixture was stirred at room temperature for 16-21 h. After addition of water (15 mL), the solid was filtered off and washed with water (2 x 10 mL). The filtrates were pooled and extracted with ethyl acetate (4 x 40 mL). The combined organic layers were washed with a 5% aqueous sodium hydrogen carbonate solution (2 x 15 mL), dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/ethanol, 9/1, v/v).

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:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, name is 3-Iodo-4-methylbenzoic acid, 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. Formula: C8H7IO2

Reference Example 8 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) benzoic acid (Compound A8) 3-Iodo-4-methyl benzoic acid (26.2 g, 100 mmol) was dissolved in DMF (300 mL), and then bis(pinacolate)diboron (38.1 g, 150 mmol), [1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (8.17 g, 10.0 mmol) and potassium acetate (49.0 g, 500 mmol) were added thereto, followed by stirring under argon atmosphere at 100C for 6 hours. To the reaction mixture was added 1 mol/L of hydrochloric acid, followed by extraction with ethyl acetate, an organic layer was washed with brine, followed by drying over anhydrous magnesium sulfate, and activated carbon (1 g) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was filtered through celite, followed by washing with ethyl acetate: The solvent was evaporated, and the resulting crystals were recrystallized from isopropyl ether, followed by filtration to obtain Compound A8 (18.5 g, 71%). 1H NMR (300 MHz, CDCl3) delta (ppm) 1.36 (s, 12H), 2.61 (s, 3H), 7.26 (d, J = 8.1 Hz, 1H), 8.02 (dd, J = 8.1, 1.8 Hz, 1H), 8.49 (d, J = 1.8 Hz, 1H).

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

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

58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, 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. name: 1-Iodo-4-methoxy-2-nitrobenzene

2-Iodo-5-methoxy-N-(4-methoxybenzyl)aniline (7f): 12 Iron (1.68 g, 30.0 mmol)was added in one portion to a stirred solution of NH4Cl (2.67 g, 500 mmol) in H2O(50 mL), and the resulting suspension was stirred at rt for 5 min. A solution of 1-iodo-4-methoxy-2-nitrobenzene (2.79 g, 10.0 mmol) in EtOH (100 mL) was then added, the resulting mixture was slowly warmed up to 60 C, and stirring was continued at this temperature for 2 h. The reaction mixture was filtered through a short pad of Celite, and the filtrate was extracted with EtOAc (3 × 50 mL). The combined organic fractions were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated to give crude 2-iodo-5-methoxyaniline (2.35 g) as a brown oil, which was used in the next step without additional purification. From this material and 4-methoxybenzaldehyde (1.28 g, 9.44 mmol), compound 7f (2.89 g, 78% overtwo steps) was obtained according to GP1b as a colorless oil, which spontaneously crystallized when stored in a freeze

The synthetic route of 58755-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rassadin, Valentin A.; Scholz, Mirko; Klochkova, Anastasiia A.; De Meijere, Armin; Sokolov, Victor V.; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 1932 – 1939;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 25245-27-6,Some common heterocyclic compound, 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, molecular formula is C8H9IO2, 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.

In a dry two necked flask were introduced N-[2-(1-Phenyl-cyclohexa-2,5-dienyl)-ethyl]-methanesulfonamide 3c (169 mg, 0.610 mmol), silver carbonate (336 mg, 1.22mmol), triphenylphosphine (24 mg, 0.092 mmol), 3,5-dimethoxy-iodobenzene 4b (322 mg, 1.22mmol), palladium acetate (6.8 mg, 0.030 mmol) and acetonitrile (24.5 mL). The mixture waswarmed to 85C and stirred for 16 hours. The mixture was filtered through celite, which wasthen washed with ethyl acetate. Evaporation of the solvents led to a paste, which was purifiedthrough silica gel chromatography (Petroleum ether/EtOAc 70:30), affording 5c as a white solid(98 mg, 39%). Mp = 123-125 C. IR (solid, KBr, numax, cm-1): 3295, 2936, 2255, 1606, 1454,1316, 1203, 1149, 1064, 973, 910, 777, 735, 710. 1H NMR (300 MHz, CDCl3): deltaH 1.53-1.63(1H, m, CHaHxCH2N), 1.90 (1H, d, 3JHH 6.0 Hz, CH cyclopropane), 1.93-2.00 (1H, m,CHaHxCH2N), 2.36 (1H, dta, JHH 6.0, 2.5 and 2.5 Hz, CH cyclopropane), 2.82 (3H, s,NSO2CH3), 3.00-3.10 (2H, m, CH2N), 3.19-3.23 (1H, m, CH cyclopropane), 3.78 (6H, s, OCH3 x2), 4.43 (1H, broad s, NH), 5.16 (1H, ddd, JHH 5.3, 2.2 and 1.5 Hz, CH olefinic), 5.91 (1H, dta, J= 5.3, 2.0 and 2.0 Hz, CH olefinic), 6.33 (1H, t, 4JHH 2.3 Hz, CH aromatic), 6.36 (1H, t, 4JHH 2.3Hz, CH x 2 aromatic), 7.17-7.35 (5H, m, 5CH aromatic). 13C NMR (75.5 MHz, CDCl3): 36.9(CH cyclopropane), 37.7 (C aliphatic), 37.9 (CH cyclopropane), 40.0 (NSO2CH3), (CH2N), 41.7(CH2CH2N), 51.3 (CH allylic), 55.4 (OCH3 x 2), 98.5 (CH aromatic), 105.8 (CH x 2 aromatic),126.6 (CH aromatic), 128.2 (CH x 2 aromatic), 131.6 (CH olefinic), 131.7 (CH x 2 aromatic),134.1 (CH olefinic), 137.5, 146.6 (2C aromatic), 160.9 (C x 2 aromatic). MS(SIMS) m/z (%):436 (M+Na, 35), 414 (M+H, 100), 305 (35). HRMS calcd for (M+H) C23H28NO4S 413.1661;found 413.1655 (1.5 ppm).

The synthetic route of 25245-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lebeuf, Raphael; Robert, Frederic; Landais, Yannick; ARKIVOC; vol. 2014; 3; (2013); p. 6 – 17;,
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. 13421-13-1, name is 4-Chloro-2-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Chloro-2-iodobenzoic acid

General procedure: The solution of 2-iodobenzoic acid (2 mmol) in thionyl chloride (2 mL) was refluxed for 1h. After completion of the reaction, the liquid was removed under reduced pressure. Then the residue was dissolved with anhydrous DCM (1 mL) and added dropwise to the mixture (DCM (1 mL), triethylamine (6 mmol) and amine (2.4 mmol) or ammonium acetate (3 mmol)). After the reaction was completed by monitoring in TLC, water (20 mL) was added to the mixture and the aqueous phase was extracted with DCM (20 mL × 3). The combined organic layers were washed with HCl (aq.2 M), saturated NaHCO3 (aq.) and brine, dried with anhydrous Na2SO4, filtered and concentrated. The crude was washed (petroleum ether/dichloromethane = 50/1, v/v) and filtered to afford 1b-x.

The synthetic route of 13421-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yingying; Zhou, Yang; Lei, Min; Hou, Jinjun; Jin, Qinghao; Guo, Dean; Wu, Wanying; Tetrahedron; vol. 75; 9; (2019); p. 1180 – 1185;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com