Category: 103440-52-4

Related Products of 103440-52-4, A common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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.

In a dry Schlenk Tube at RT under nitrogen are successively charged 2-iodo-5-methylbenzoic acid methyl ester (13.765 mmol, 1 eq), Cul (2.753 mmol, 0.2 eq), CsF (27.529 mmol, 2 eq), 2-tributylstannylpyridine (20.647 mmol, 1.5 eq), Pd(PPh3)4 (1.376 mmol, 0.1 eq) and DMF (60 mL). The resulting suspension is stirred at 90C overnight. The obtained reaction mixture is diluted with EtOAc and filtered through a short pad of Celite. A solution of sat. aq. NaHC03 is then added to the filtrate and the aq. phase extracted with EtOAc (3 times). The combined organic layers are washed with H20 and brine, dried over Na2S04, filtered and concentrated under reduced pressure. Purification is achieved by FC (EtOAc/Heptane 1 :4 to 3:7) to give methyl 5-methyl-2-(pyridin-2-yl)benzoate as a brown oil. LC-MS (conditions B): tR = 0.67 min, [M + 1]+ = 228.07.

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; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BROTSCHI, Christine; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi, T.; WO2013/50938; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4, The chemical industry reduces the impact on the environment during synthesis 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, I believe this compound will play a more active role in future production and life.

Methyl 5-methyl-2~(4 A5.54etramethyl- 1 ,3.2-dioxaborolan-2-yDbenzoate (B-2)A solution of B4 (5.9 kg, 21.37 mol) in iPAc was charged in a visually clean 100 L reactor equipped with a mechanical stirrer and thermocouple. The solution was solvent switched to 2-MeTHF (-35 L). Triethylamine (8.94 L5 64.1 mol) was added and the solution was degassed with N2- Pinacol borane (4.65 L, 32.1 mol) was added slowly (over 15 mins) to the stirring solution while maintaining the purge. The solution was further degassed for 10 min and tri-o-tolylphosphine (0.325 kg, 1.069 mol) was added followed by palladium (II) acetate (0.120 kg, 0.534 mol). This caused the reaction to turn black immediately with a slow exotherm from 11.5 0C to 30 0C. At this point a delayed exotherm was observed and the reaction temperature increased to 60 0C (over 45 min). The reaction temperature was increased to 77 0C and aged for another 45 min. At this point, HPLC analysis of a reaction aliquot revealed complete consumption of the starting material. The heat source was removed and an ice bath was placed under the flask to cool the reaction over 1.5 h. A 26 w% ammonium chloride solution was added very slowly to control gas evolution and exotherm (over 60 minutes) which caused a black precipitated to form. The supernatant was transferred to an extractor which already contained 40 L of water. The black slurry remaining was filtered on Solka-Floc and washed with MTBE (-20 L). The filtrate was loaded into the extractor. The layers were cut and assay of the organic layers revealed R-2 (4.45 kg, 16.11 mol, 75 % yield) in 81.6% purity and was used as is in the following step. lH NMR (500 MHz, CDC13, 293K, TMS); 7.75 (1 H, s), 7.40 (1 H, d, J = 7.49 Hz), 7.32 (1 H, d, J = 7.56 Hz)5 3.90 (3 H, s), 2.37 (3 H5 s), 1.41 (12 H5 s).

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, Methyl 2-Iodo-5-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; MERCK FROSST CANADA LTD.; WO2009/143033; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4,Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (10 mg, 0.05 mmol, 10 mol%), K2CO3 (276 mg, 2.0 mmol), 1,10-phenanthroline (20 mg, 0.10 mmol, 20 mol%) and cyclic thiourea (0.5 mmol), 4 ? Molecular Sieves. The tube was evacuated and backfilled with N2 (this procedure was repeated 3 times). Under a counter flow of N2, methyl-2-iodobenzoate 1 (0.6 mmol) and DMF (2.0 mL) were added by syringe. The mixture was stirred at 100 ºC for 24h. After the reaction was completed, the mixture was directly passed through celite and rinsed with 30 mL of EtOAc. The combined filtrate was concentrated and purified by column chromatography on silica gel to give the pure product.Yellow Yellow solid; mp 126-128 C; 1H NMR (400 MHz, CDCl3) delta 8.04 (s, 1H), 7.31 (d, J = 7.6 Hz,1H), 7.12 (d, J = 8.0 Hz,1H), 3.52-3.45 (m, 1H), 3.28-3.22 (m, 1H), 3.12-3.09 (m, 1H), 2.38-2.36 (m, 4H), 1.91 (s, 2H), 1.72-1.63 (m, 1H), 1.56-1.43 (m, 3H); 13C NMR (50 MHz, CDCl3) delta 162.5, 154.8, 137.0, 134.5, 130.9, 128.6, 125.2, 124.5, 71.7, 67.5, 31.1, 30.9, 25.4, 25.0, 21.1 ppm. Anal. Calcd. for C15H16N2OS: C 66.15, H 5.92, N 10.29; found: C 66.21, H 5.70, N 10.37; EI-MS: m/z = 272 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-Iodo-5-methylbenzoate, its application will become more common.

Reference:
Article; Chen, Dingben; Wu, Jiashou; Yang, Jianguo; Huang, Ling; Xiang, Yubo; Bao, Weiliang; Tetrahedron Letters; vol. 53; 52; (2012); p. 7104 – 7107;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 103440-52-4, 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. 103440-52-4 name is Methyl 2-Iodo-5-methylbenzoate, 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.

A degasssed mixture of ester EX-25A (10.35 g, 0.037 mol)), Pd(dba)3 (0.017 g, 0.018 mmol)), dppf (0.025 g, 0.045 mmol)) and Zn(CN)2 (2.6 g, 0.02 mol) in DMF (100 mL) was heated to 120 C. for 2 hours. The reaction mixture was poured into water and ethyl acetate. The organic layer was washed with water (2) and brine (1). The organic layer was collected, dried (MgSO4) and the solvent removed in vacuo to give 5.28 g methyl 2-cyano-5-methylbenzoate (EX-25B) as a brownish oil with m/z+1=176.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-Iodo-5-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Pharmacia Corporation; US6664255; (2003); B1;,
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. 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, A new synthetic method of this compound is introduced below., COA of Formula: C9H9IO2

Step (ii); 2-Butoxy-9-(4-iodo-3-methoxycarbonylbenzyl)-8-methoxyadenine; [Show Image] To 4-iodo-3-methoxycarbonyltoluene 1.7 g (6.2mmol) obtained in step (i) in carbon tetrachloride (30ml) were added NBS 1.2g (6.8mmol) and perbenzoic acid 100mg, and the mixture was stirred at 90C for 6.5 hours. After filtration and concentration, to the residue was added water and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine, dried over Na2SO4 and concentrated. The residue dried in vacuo was dissolved in DMF (30ml). Thereto were added 2-butoxy-8-methoxyadenine, trifluoroacetic acid 1.73g (4.9mmol) and potassium carbonate 1.7g (12.3mmol) and the mixture was stirred at room temperature for 13 hours. After filtration and concentration, to the residue was added water, and the mixture was extracted with chloroform-methanol. The organic layer was washed with water and saturated brine, dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the titled compound 620mg (1.2mmol) as a reddish brown oil. Yield 25% 1H NMR (DMSO-d6) delta 7.97 (1H, d, J = 8.2 Hz), 7.64 (1H, brs), 7.10 (1H, d, J = 8.2 Hz), 6.87 (2H, brs), 5.04 (2H, s), 4.15 (2H, t, J = 6.6 Hz), 4.05 (3H, s), 3.83 (3H, s), 1.65-1.61 (2H, m), 1.40-4.35 (2H, m), 0.92 (3H, t, J = 7.4 Hz).

The synthetic route of 103440-52-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; AstraZeneca AB; EP1939202; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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. Recommanded Product: 103440-52-4

STEP-7: To a stirred solution of compound-7 (1.0 eq) in 20 Vol of carbon tetrachloride and added N-bromosuccinimide (1.1 eq) followed by catalytic amount of benzoyl peroxide (0.1 eq). Reaction mixture was later refluxed for 24 h. The reaction mixture was filtered to remove succinmide and the filtrate was washed with brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure. Crude residue was purified by silica gel chromatography Results: TABLE 7 1H NMR (CDCl3, 400 MHz) delta splitting pattern and J value Protons Group 7.63 d 1 H ArH 7.54 d 1 H ArH 7.04 d 1 H ArH 4.56 s 2 HCH2Br 3.88 s 3 HOCH3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103440-52-4, its application will become more common.

Reference:
Patent; KRISANI BIOSCIENCES (P) LTD; US2011/281893; (2011); 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. 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 103440-52-4

General procedure: This kind of general experimental procedure is based on our already published procedure.13 The general procedure (GP) was carried out with ortho-iodoester 1a-d (105.0-136.0 mg, 0.40 mmol) and aldehyde 2a-k (195.0-313.0 mg, 1.6 mmol) in the presence of Pd(OAc)2 (5.0 mg, 5 mol%), Ag2O (111.3 mg, 0.48 mmol), and TBHP (257.1 mg, 2.0 mmol) allowing the reaction mixture to stir at 120 C for 12-20 h. Progress of the reaction was monitored by TLC until the ortho-iodoester 1a-d had completely reacted. Then the reaction mixture was removed from the oil bath and allowed to reach r.t. DCE (2 mL) and concd H2SO4 (1.0 mL) were added and the mixture was stirred at 60 C for 5 min to 2 h. Progress of the product formation was monitored by TLC until the reaction was complete. The mixture was quenched by the addition of aq NaHCO3 and then extracted with CH2Cl2 (3 * 15 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (PE/EtOAc) furnished the products 3 (57.0-86.0 mg, 55-69%). The products 3aa, 3ac, 3ai, 3aj, 3ak, 3ba, 3bc, 3be, and 3bj are reported in the literature.9

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; Suchand, Basuli; Satyanarayana, Gedu; Synthesis; vol. 51; 3; (2019); p. 769 – 779;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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. Product Details of 103440-52-4

General procedure: This kind of general experimental procedure is based on our already published procedure.13 The general procedure (GP) was carried out with ortho-iodoester 1a-d (105.0-136.0 mg, 0.40 mmol) and aldehyde 2a-k (195.0-313.0 mg, 1.6 mmol) in the presence of Pd(OAc)2 (5.0 mg, 5 mol%), Ag2O (111.3 mg, 0.48 mmol), and TBHP (257.1 mg, 2.0 mmol) allowing the reaction mixture to stir at 120 C for 12-20 h. Progress of the reaction was monitored by TLC until the ortho-iodoester 1a-d had completely reacted. Then the reaction mixture was removed from the oil bath and allowed to reach r.t. DCE (2 mL) and concd H2SO4 (1.0 mL) were added and the mixture was stirred at 60 C for 5 min to 2 h. Progress of the product formation was monitored by TLC until the reaction was complete. The mixture was quenched by the addition of aq NaHCO3 and then extracted with CH2Cl2 (3 * 15 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (PE/EtOAc) furnished the products 3 (57.0-86.0 mg, 55-69%). The products 3aa, 3ac, 3ai, 3aj, 3ak, 3ba, 3bc, 3be, and 3bj are reported in the literature.9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 103440-52-4, its application will become more common.

Reference:
Article; Suchand, Basuli; Satyanarayana, Gedu; Synthesis; vol. 51; 3; (2019); p. 769 – 779;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 103440-52-4, These common heterocyclic compound, 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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.

Add 1.65 g (10 mmol) to a 250 mL round bottom flask.2-Amino-5-methylbenzoic acid methyl ester, 6.07 g (22 mmol)Methyl 2-iodo-5-methylbenzoate, 3.32 g (24 mmol) potassium carbonate,0.26 g (4 mmol) of activated copper powder and 100 mL of o-dichlorobenzene,Degas the reaction system and then protect it with argon.The mixture was heated to 180 C with stirring and the reaction was continued for 72 h. After the reaction is complete,The system was cooled to room temperature, suction filtered under reduced pressure and the residue was washed with dichloromethane.After the filtrate is dried,With dichloromethane:The petroleum ether = 4:1 (volume ratio) eluent was separated and purified on a silica gel column.Obtained a yellow solid 3.38g,The yield was 73.2%.

Statistics shows that Methyl 2-Iodo-5-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 103440-52-4.

Reference:
Patent; Soochow University (Suzhou); Liao Liangsheng; Yuan Yi; Jiang Zuoquan; (46 pag.)CN109456326; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 103440-52-4, name is Methyl 2-Iodo-5-methylbenzoate, 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 103440-52-4, Product Details of 103440-52-4

In a dry Schlenk Tube at RT under nitrogen are successively charged 2-iodo-5- methylbenzoic acid methyl ester (13.765 mmol, 1 eq), Cul (2.753 mmol, 0.2 eq), CsF (27.529 mmol, 2 eq), 2-tributylstannylpyridine (20.647 mmol, 1.5 eq), Pd(PPh3)4 (1.376 mmol, 0.1 eq) and DMF (60 ml_). The resulting suspension is stirred at 90C overnight. The obtained reaction mixture is diluted with EtOAc and filtered through a short pad of Celite. A solution of sat. aq. NaHC03 is then added to the filtrate and the aq. phase extracted with EtOAc (3 times). The combined organic layers are washed with H20 and brine, dried over Na2S04, filtered and concentrated under reduced pressure. Purification is achieved by FC (EtOAc/Heptane 1 :4 to 3:7) to give methyl 5-methyl-2-(pyridin-2-yl)benzoate (2.64 g) as a brown oil. LC-MS (conditions A): tR = 0.67 min, [M + 1 ]+ = 228.07.

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; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BROTSCHI, Christine; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2012/85857; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com