Category: 1829-28-3

Synthetic Route of 1829-28-3, 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. 1829-28-3, name is Ethyl 2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

To a 2-dram vial with a PTFE-lined cap was charged with acetal 1f (1.00 mL, 0.100 M in DCE, 0.100 mmol), ethyl 2-iodobenzoate (111 mg, 0.402 mmol), NBE-CO2Me (23.8 mg, 0.157 mmol), Pd(TFA)2 (3.4 mg, 0.0102 mmol), TFA-Gly-OH (3.4 mg, 0.0199 mmol), AgOAc (66.3 mg, 0.397 mmol), and DCE (1.00 mL). The resulting mixture was heated to 100° C. and stirred for 24 h. After cooling to room temperature, ethylenediamine (0.100 mL) was added, and the resulting mixture was stirred at 23° C. for 2 h. The mixture was filtered through a plug of silica gel, eluting with EtOAc (30 mL), and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (3:1 hexanes/EtOAc eluent) to afford arylation product 3fp (35.4 mg, 62percent yield, Rf=0.16 in 2:1 hexanes/EtOAc) as a colorless oil. 1H NMR: (500 MHz, CDCl3) delta 8.16 (d, J=8.5 Hz, 1H), 8.05 (s, 1H), 7.84 (d, J=8.2 Hz, 1H), 7.79 (d, J=7.7 Hz, 1H), 7.75-7.68 (m, 1H), 7.59-7.54 (m, 1H), 7.49 (app. td, J=7.5, 1.2 Hz, 1H), 7.42-7.33 (m, 2H), 7.28 (s, 1H), 7.20 (s, 1H), 7.07 (s, 1H), 6.32 (s, 1H), 5.40 (d, J=13.2 Hz, 1H), 5.23 (d, J=13.2 Hz, 1H), 4.96 (d, J=11.6 Hz, 1H), 4.86 (d, J=11.6 Hz, 1H), 4.03 (q, J=7.1 Hz, 2H), 3.69 (q, J=7.1 Hz, 2H), 1.40 (s, 9H), 1.15 (t, J=7.1 Hz, 3H), 0.95 (t, J=7.1 Hz, 3H). 13C NMR: (100 MHz, CDCl3) delta 168.9, 159.5, 154.6, 148.6, 142.5, 142.1, 141.8, 138.2, 131.5, 131.3, 130.8, 130.7, 129.92, 129.90, 129.7, 129.1, 128.07, 128.05, 127.5, 127.3, 126.3, 125.8, 125.5, 103.7, 80.2, 70.1, 70.0, 61.1, 45.2, 28.5, 14.1, 13.9. IR: (film) 1698, 1290, 1253, 1151, 758 cm?1.HRMS: (ESI+) m/z calc’d for (M+H)+ [C34H36N2O6+H]+: 569.2646, found 569.2651.

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

Reference:
Patent; The University of Georgia Research Foundation, Inc; Ferreira, Eric; Li, Qiankun; (47 pag.)US2018/65909; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

General procedure: Hydrazides (30?58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3?6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).

The synthetic route of 1829-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mehr-Un-Nisa; Munawar, Munawar A.; Chattha, Fauzia A.; Kousar, Samina; Munir, Jawaria; Ismail, Tayaba; Ashraf, Muhammad; Khan, Misbahul A.; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 6014 – 6024;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1829-28-3, A common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

[00319] 25.5 mg of PdCl2[dppf].CH2Cl2 was placed in a reaction tube under nitrogen and added 4 ml dioxane and 0.45 ml triethylamine. The mixture was heated at 80 C. for 23 h to give a brownish solution. To this solution was then added 286 mg (1.04 mmol) of ethyl 2-iodobenzoate and 0.23 ml (1.6 mmol) pinacolborane. The reaction mixture was heated with stirring to 80 C. for 16.5 h and then analysed by gc and the products identified by gc/ms. The gc solutions were prepared by washing an aliquot of the reaction solution dissolved in ethyl acetate with water and dried. The reaction was finished, the desired product peak in the gc had an area of 84percent with the only other significant peak being that due to the dehalogenation product, ethyl benzoate (14percent).

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; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 1829-28-3, name is Ethyl 2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 2-iodobenzoate

To a 2-dram vial with a PTFE-lined cap was charged with acetal 1o (30.1 mg, 0.0980 mmol), ethyl 2-iodobenzoate (111 mg, 0.402 mmol), NBE-CO2Me (23.1 mg, 0.152 mmol), Pd(TFA)2 (3.3 mg, 0.00994 mmol), TFA-Gly-OH (3.3 mg, 0.0193 mmol), AgOAc (66.0 mg, 0.395 mmol), and DCE (2.00 mL). The resulting mixture was heated to 100° C. and stirred for 24 h. After cooling to room temperature, ethylenediamine (0.100 mL) was added, and the resulting mixture was stirred at 23° C. for 2 h. The mixture was filtered through a plug of silica gel, eluting with EtOAc (30 mL), and the filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC (2:1 hexanes/EtOAc eluent) to afford arylation product 3opmono (13.6 mg, 30percent yield, Rf=0.21 in 2:1 hexanes/EtOAc) as a yellow oil and arylation product 3opdi together with an unidentified impurity (6.0 mg total). (20percent recovery of starting material 1o was also observed in the crude NMR prior to purification.) The impure arylation product 3opdi was then dissolved in MeOH (2.00 mL), HCl (gas) was bubbled through the mixture until the pH 1, and the mixture was stirred at room temperature for 23 h. Saturated aq. Na2CO3 (5 mL) and water (10 mL) were then added, and the mixture was extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine (15 mL) and dried over anhydrous Na2SO4. The solvent was concentrated by rotary evaporation, and the resulting residue was purified by preparative TLC (2:1 hexanes/EtOAc eluent) to afford biaryl alcohol 6opdi (3.3 mg, 8percent yield, Rf=0.21 in 2:1 hexanes/EtOAc) as a colorless oil. Monoarylation product (3opmono): 1H NMR: (400 MHz, CDCl3) delta 8.17 (d, J=8.5 Hz, 1H), 8.05 (s, 1H), 7.86 (d, J=7.2 Hz, 1H), 7.83 (d, J=8.2 Hz, 1H), 7.72 (app. t, J=7.7 Hz, 1H), 7.61-7.48 (m, 2H), 7.46-7.30 (m, 4H), 6.86 (d, J=8.4 Hz, 1H), 6.32 (s, 1H), 5.40 (d, J=13.2 Hz, 1H), 5.23 (d, J=13.2 Hz, 1H), 4.93 (d, J=11.1 Hz, 1H), 4.85 (d, J=11.1 Hz, 1H), 4.07 (q, J=7.2 Hz, 2H), 3.69 (s, 3H), 1.02 (t, J=7.2 Hz, 3H). 13C NMR: (100 MHz, CDCl3) delta 168.5, 159.7, 156.1, 148.6, 138.7, 132.1, 131.63, 131.56, 130.83, 130.80, 130.6, 129.93, 129.85, 129.64, 129.56, 129.2, 129.1, 128.1, 128.0, 127.3, 127.2, 110.2, 103.4, 70.2, 70.1, 60.8, 55.5, 14.0. IR: (film) 1721, 1503, 1289, 1251, 1020 cm?1. HRMS: (ESI+) m/z calc’d for (M+H)+ [C28H25NO5+H]+: 456.1805, found 456.1813. Diarylation product alcohol (6opdi): 1H NMR: (400 MHz, CDCl3) delta 7.90 (d, J=7.8 Hz, 2H), 7.57-7.49 (m, 2H), 7.46-7.38 (m, 4H), 7.22 (s, 2H), 4.69 (d, J=5.9 Hz, 2H), 4.17 (app. br. s, 4H), 3.01 (s, 3H), 1.66 (t, J=5.9 Hz, 1H), 1.12 (t, J=7.0 Hz, 6H). 13C NMR: (125 MHz, CDCl3) delta 168.2, 153.7, 139.0, 136.0, 135.2, 131.6, 131.3, 129.9, 128.6, 127.5, 65.2, 61.0, 60.1, 14.1. IR: (film) 3473, 1717, 1291, 1254, 1131 cm?1.HRMS: (ESI+) m/z calc’d for (M+Na)+ [C26H26O6+Na]+: 457.1622, found 457.1627.

According to the analysis of related databases, 1829-28-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The University of Georgia Research Foundation, Inc; Ferreira, Eric; Li, Qiankun; (47 pag.)US2018/65909; (2018); 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. 1829-28-3, name is Ethyl 2-iodobenzoate, A new synthetic method of this compound is introduced below., Safety of Ethyl 2-iodobenzoate

0.54 g (5 mmol) of 2.76 g (10 mmol) of o-phenylenediamine and ethyl iodobenzoate were weighed into a microwave reaction tube, and cuprous iodide (80 mg, 0.5 mmol), potassium phosphate (3.18 g, 15 mmol), Then, an appropriate amount of ethylene glycol and magnetron were added to the microwave reaction tube, and the microwave reaction was carried out under the protection of nitrogen at 180 C. After 1 h, the reaction was stopped, and the TLC detection was completed. Ethyl acetate (3 × 100 mL) and an appropriate amount of water and saturated NaCl solution were extracted, the organic layer was combined, an appropriate amount of anhydrous Na 2 SO 4 was added to remove water, suction filtration, and the filtered liquid was concentrated, and 1 g of silica gel was added for mixing.Separated using silica gel column chromatography,The eluent was (dichloromethane/methanol = 100/1) to give a bright yellow solid, 3, 0.68 g, yield 65%.

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; Xinxiang Medical University; Xinxiang Medical School San Quan College; Yan Fulin; Wang Yawen; Yan Jianwei; Yin Tiantian; Ma Jinshuo; (15 pag.)CN110183387; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 1829-28-3, The chemical industry reduces the impact on the environment during synthesis 1829-28-3, name is Ethyl 2-iodobenzoate, I believe this compound will play a more active role in future production and life.

In a test tube equipped with a stirrer and a septum cap, trifluoromethylzinc iodide (DMPU) 2 complex (160 mg, 0.2 mmol) prepared in Example 1 and copper (I) iodide (1.9 mg, 0.01 mmol ) Was charged, and argon substitution was carried out three times. Then, a solution of ethyl 2-iodobenzoate (16.6 mul, 0.1 mmol) in DMPU (0.2 ml) was added, the septum cap was replaced with a screw chap, and the reaction was carried out at 50 ° C. for 24 hours. After completion of the reaction, the reaction solution was quantified with 19 F-NMR (benzotrifluoride internal standard), and ethyl 2-trifluoromethylbenzoate was produced with a yield of 80percent

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:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; TOSOH F-TECH INCORPORATED; MIKAMI, MIKAMI; NAKAMURA, YUZO; NEGISHI, KAZUYUKI; AIKAWA, KOHSUKE; (8 pag.)JP5889817; (2016); B2;,
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. 1829-28-3, name is Ethyl 2-iodobenzoate, A new synthetic method of this compound is introduced below., Product Details of 1829-28-3

To a dried pressure tube was added o-phenylenediamine (0.3 g, 2.7 mmol), ethyl-2-iodobenzoate (1.5 g, 5.5 mmol) under nitrogen followed by ethylene glycol (6 mL), 10 mol % CuI (52 mg, 0.27 mmol) and K3PO4 tribasic (1.17 g, 5.5 mmol). Pressure tube was closed tightly and heated at 100 C for 4 h. After completion of the reaction (monitored by TLC) reaction mixture was cooled to room temperature and filtered over a pad of silica with CH2Cl2 to remove CuI and base residues. Then solvent was removed on rotary evaporator and the residue was purified on silica column chromatography using 25-30% EtOAc in hexane as solvent to give 1 Yield 50% (0.29 g). (0019) mp: 251-253 C; IR (upsilonmax):3320, 3025, 1603, 1579, 1471, 1394, 1157, 748 cm-1; 1H NMR (300 MHz, DMSO-d6): delta 8.63 (s, 1H, Amide NH), 6.60 (s, 1H, Amine NH), 6.46 (dd, J = 7.9, 1.4 Hz, 1H, ArH), 6.19-6.08 (m, 1H, ArH), 5.87-5.63 (m, 6H, ArH);13CNMR (75 MHz, DMSO): delta 168.1, 150.4, 140.0, 133.2, 131.9, 129.6, 124.6, 123.0, 122.7, 121.2, 120.9, 119.8, 119.0; HRMS (ESI) m/z calculated for [M+H]+ [C13H11N2O] 211.0866, found 211.0860.

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; Praveen Kumar, Chintakunta; Reddy, T. Srinivasa; Mainkar, Prathama S.; Bansal, Vipul; Shukla, Ravi; Chandrasekhar, Srivari; Huegel, Helmut M.; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 674 – 686;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1829-28-3, A common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

General procedure: A dry and argon-flushed Schlenk tube, equipped with a magnetic stirring bar and a rubber septum was charged with Ni(acac)2 (12.8 mg, 0.05 mmol, 0.05 equiv) as catalyst, 4-fluorostyrene (24.4 mg, 0.20 mmol, 0.20 equiv), the aryl iodide or heteroaryl chloride 3 as electrophile (1.00 mmol, 1.00 equiv), and freshly distilled THF (1 mL). The resulting suspension was cooled to 0 °C and the prior prepared benzylic manganese chloride solution (1.20 mmol, 1.20 equiv) was added dropwise at the prior adjusted temperature. The reaction conversion was monitored by GC analysis of hydrolyzed aliquots. After full conversion of the selected electrophile, the reaction mixture was quenched with a sat. aq NH4Cl and extracted with EtOAc (3 × 75 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. Purification of the crude product by flash column chromatography afforded the desired products.

The synthetic route of 1829-28-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Benischke, Andreas D.; Desaintjean, Alexandre; Juli, Thomas; Cahiez, Gerard; Knochel, Paul; Synthesis; vol. 49; 24; (2017); p. 5396 – 5412;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

Weighing 5.52 g (20 mmol) of o-iodobenzoic acid ethyl ester obtained by esterification of o-iodobenzoic acid with anhydrous ethanol in a microwave reaction tube, 1.08 g (10 mmol) of o-phenylenediamine.Add copper iodide (190 mg, 1 mmol) in turn,Potassium phosphate (6.36g, 30mmol),Appropriate amount of ethylene glycol and magnetron at 180 C,Microwave reaction under nitrogen protection,The reaction was stopped after 1 h, and the reaction was terminated by TLC. Extraction with ethyl acetate (3 x 100 mL),Wash with water and an appropriate amount of saturated brine, combine the organic layers, add anhydrous Na2SO4 to remove water,After filtration, the residue was concentrated and the residue was purified by column chromatography to yield 1.The yield of the obtained Compound 1 was 65%.

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

Reference:
Patent; Xinxiang Medical University; Yan Fulin; Cao Ke; Yan Jianwei; Ma Lijuan; Lv Haixia; Wang Yawen; Yin Tiantian; (25 pag.)CN108586364; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 1829-28-3,Some common heterocyclic compound, 1829-28-3, name is Ethyl 2-iodobenzoate, molecular formula is C9H9IO2, 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.

General Procedures for Synthesis of 5-Aryl-2-Furaldehydes (5). 5-Aryl-2-furaldehyde 5 was synthesized from Suzuki coupling of 5-formyl-2-furanboronic acid and corresponding aryl halides 4 in 72-75percent yields following a literature procedure (Scheme 3) (Hosoya, et al. (2003) Bioorg. Med. Chem. 11:663). The crude solid products were purified by column chromatography using dichloromethane as eluent. wherein R2 is 2-NO2, 3,4-diMe (4a, 5a); H (4b, 5b); 4-NO2 (4c, 5c); 2-COOEt (4d, 5d).

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

Reference:
Patent; Marmorstein, Ronen; Liu, Xin; Cole, Philip A.; Wang, Ling; Bowers, Erin M.; Meyers, David J.; Mukherjee, Chandrani; US2010/216853; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com