Category: 71838-16-9

Application of 71838-16-9, These common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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.

Step 1: to a solution of 2-bromo-1-iodo-4-methylbenzene (1.74 g, 5.86 mmol) indry THF (20 mL) was added a solution of isopropylmagnesium chloride 2 M inTHF (2.93 mL, 5.86 mmol) at -40C. Then, 2-methyl-N-[(5-methylfuran-2-yl)methylidene]propane-2-sulfinamide Ex.lla (1.00 g, 4.69 mmol) diluted in dryTHF (5 mL) was added dropwise at -40C. The reaction was warmed to rt and stirred at that temperature for 3 days. Water was added to quench the reaction. The two layers were partitionated and the organic layer was dried over Mg504, filtered and the solution was concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using a gradient of hexanes/EtOAc ([8:2] to [6:4]) to afford N-[(2-bromo-4-methylphenyl)(5- methylfuran-2-yl)methyl]-2-methylpropane-2-sulfinamide Ex.12a (541 mg, 30%).

The synthetic route of 71838-16-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; BONNET, Pascal; FOGHA, Jade; (144 pag.)WO2018/138359; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

71838-16-9, 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. 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, A new synthetic method of this compound is introduced below.

General procedure: To a solution of benzenethiol (0.6 mmol) in DMSO (2 mL) was added in a Schlenk tube at room temperature under oxygen condition. Subsequently, Cs2CO3 (1.0 mmol), CuI (0.02 mmol) and 1-bromo-2-iodobenzene (0.5 mmol) were added. The mixture was heated under 95 C for 4 h. After the reaction was completed, cooled to room temperature. Water (10 mL) was added to the reaction mixture and CH2Cl2 (3×10 mL) were used to extract the crude product. After removing the solvent, the resulting crude was purified by column chromatography with pure petroleum as eluent to give 1 as Colorless oily liquid.

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; Liu, Na; Chao, Fei; Huang, Yu; Wang, Yanlan; Meng, Xu; Wang, Long; Liu, Xiang; Tetrahedron Letters; vol. 60; 46; (2019);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 71838-16-9, 71838-16-9

The cadmium reagent was generated as in Example 1 using Cd metal (8.5 g, 0.075 mole), diethyl bromodifluoromethylphosphonate (18 g, 0.068 mole) and AcOH (1.0 niL) in DMF (80 mL). A 40 mL aliquot of this solution was added to CuCl (6.72 g, 0.068 mole) followed after 2 minutes by the addition of 3-bromo-4-iodotoluene (5.0 g, 0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with additional ether (300 mL) and the combined ether layer was washed with saturated ammonium chloride (500 mL) and water (500 mL) then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/ hexanes afforded 4.4 g of (2-bromo-4-methyl-phenyl)difluoromethylphosphonic acid diethyl ester. To the diethyl ester material obtained, (1.8 g, 0.005 mole) in carbon tetrachloride (CCl4, 30 mL), were added AIBN (0.033 g, 0.0002 mole) and N- bromosuccinimide (NBS, 0.89 g, 0.005 mole). The reaction was heated at reflux for 2 hours (a thin white suspension formed). The reaction was allowed to reach room temperature and the solvent was removed under vacuum. The residue was taken up in ethyl acetate (EtOAc, 120 mL) and washed with saturated NaHCtheta3 (60 mL) and brine (60 mL) then dried over MgSO4. Filtration and solvent evaporation afforded 2.1 g of crude product. Flash chromatography on silica gel using 20-30% ethyl acetate/hexanes afforded 1.11 g of (2- bromo-4-bromomethyl-phenyl)-difluoro-methylphosphonic acid diethyl ester.; Example 25 – Synthesis of Compound 25(2-Bromo-4-methylphenyl) difluoromethylphosphonic acid diethyl ester 25 To a suspension of 8.5 g Cd metal (0.075 mole), in 80 mL DMF (dried over 4A molecular sieves for 24 hours) was added 18 g of diethyl bromodifluoro-methylphosphonate (0.068 mole) and 1 mL glacial acetic acid. Within 4 minutes an exotherm started and lasted EPO ? for 20 minutes. The suspension was stirred for 3 hours and allowed to stand at room temperature for 30-40 minutes. A 40 mL aliquot of this solution was added to 6.72 g of CuCl (0.068 mole) followed after 2 minutes by the addition of 5 g of 3-bromo-4-iodotoluene (0.017 mole). The reaction suspension was stirred for 28 hours, then more cadmium reagent solution (30 mL) was added and the reaction stirred an additional 4 days. Ether (700 mL) was added and the solution was filtered through Celite. The Celite cake was washed with 300 mL of ether and the combined ether layer was washed with 500 mL of saturated ammonium chloride and 500 mL of water, then dried over magnesium sulfate. Filtration and solvent evaporation left behind 8.5 g of crude product. Flash chromatography on silica gel using 30% ethyl acetate/hexanes afforded 4.4 g of Compound 25.

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-Bromo-1-iodo-4-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CEPTYR, INC.; WO2006/55525; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 71838-16-9. 71838-16-9

General procedure: Et2NH (20 mL), THF (20 mL), 1-bromo-2-iodobenzene (2.2 mL g,18 mmol), and trimethylsilylacetylene (2.9 mL, 21 mmol) weresuccessively added to a flask containing PdCl2(PPh3)2 (0.25 g,0.35 mmol) and CuI (0.067 g, 0.35 mmol). The mixture was stirredat room temperature for 12 h and then evaporated. The residuewasdiluted with hexane/AcOEt (5:1) and washed with 1M aqueousHCl. The organic layer was dried over Na2SO4 and evaporated. Purificationof the residue by silica-gel column (hexane) gave 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzene [38274-16-7] (1a?) asa pale yellow clear liquid (4.12 g, 16.3 mmol, 92% yield).nBuLi (2.65M in hexane, 701 mL, 1.86 mmol) was added to astirred solution of 1a? (472 mg, 1.86 mmol) in THF (4 mL) at 78 C.After 0.5 h, Me2SiCl2 (223 mL, 1.86 mmol) was added to the mixtureat that temperature. Then the mixture was warmed to room temperatureand stirred for 2 h. MeOH (0.5 mL) and Et3N (290 mL,2.08 mmol) were successively added to the reaction mixtureat 78 C. After removing the cooling bath, the resultant mixturewas stirred at room temperature for 1 h. The mixturewas quenchedwith water and extracted with hexane/AcOEt (30:1) three times.The combined organic layer was dried over Na2SO4 and evaporated.The residuewas purified by flash column chromatography (hexane/AcOEt 40:1). The title compound,1-(methoxydimethylsilyl)-2-[2-(trimethylsilyl)ethynyl]benzene (1a), was obtained as a pale yellowliquid (0.721 g, 2.75 mmol, 71% yield). 1H NMR (500 MHz, CDCl3,7.26 ppm) d 0.25 (s, 9H), 0.47 (s, 6H), 3.56 (s, 3H), 7.30e7.34 (m, 2H),7.48e7.50 (m, 1H), 7.59e7.61 (m, 1H); 13C NMR (125 MHz, CDCl3,77.0 ppm) d 1.8, 0.3, 50.9, 96.9, 106.4, 127.7, 127.7, 129.2, 132.8,134.0, 140.8; IR (neat) 3073, 3052, 2959, 2831, 2155, 1429 cm1;HRMS (EI) calcd for C14H22OSi2 [M] 262.1209, found 262.1209.The substrates 1b-l, and 1p were synthesized by the samemanner as described for the preparation of 1a.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Bromo-1-iodo-4-methylbenzene.

Reference:
Article; Kinoshita, Hidenori; Fukumoto, Hiroki; Ueda, Akihiro; Miura, Katsukiyo; Tetrahedron; vol. 74; 14; (2018); p. 1632 – 1645;,
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 71838-16-9 as follows. 71838-16-9

General procedure: A mixture of carbazole(1.67 g, 10 mmol), 2-bromoiodobenzene (4.2 g, 15 mmol), K2CO3 (2.76 g, 20 mmol), CuI (0.95 g, 5 mmol) and DMA (100 mL) in a 250 mL three-necked flask was heated at 130 C for 48 h under nitrogen. After cooling, it was poured into water (200 mL) and extracted with CH2Cl2, the combined organic phase was washed with water and dried over MgSO4. After workup, the crude product was isolated by column chromatography (PE) to afford white powder.

According to the analysis of related databases, 71838-16-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lv, Jun; Liu, Qiancai; Tang, Jie; Perdih, Franc; Kranjc, Kristof; Tetrahedron Letters; vol. 53; 39; (2012); p. 5248 – 5252;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

71838-16-9, These common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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.

[(2-Bromo-4-methyl-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester: A solution of (bromo-difluoro-methyl)-phosphonic acid diethyl ester (25.00 g, 93.6 mmol) in N,N-dimethylacetamide (50 mL) was added drop wise into a suspension of activated zinc (6.12 g, 93.6 mmol) under Argon. The reaction was initiated by heating and kept under 50 C. After the mixture was stirred for 3 h, copper (I) bromide (13.43 g, 93.6 mmol) was added and stirred for 1 h. A solution of 2-bromo-l-iodo-4-methyl-benzene (11.88 g, 40.0 mmol) in N,N-dimethylacetamide (25 mL) was added slowly to the reaction mixture. The resulting suspension was then stirred at room temp for 18 h. Water (100 mL) was added to the reaction mixture and the solution filtered through celite. The filtrate was diluted with EtOAc (250 mL) and organic layer was washed with H20 (50 mL), NaHC03 (5%, 50 mL) and H20 (50 mL). The solvent was removed and the residue was purified by column chromatography on silica gel, eluting with hexanes/EtOAc (4:1) to provide a colorless oil (11.75 g, 82%): .H NMR (300 MHz, CDC13) 8 7.51 (d, 1H), 7.49 (s, 1H), 7.19 (d, 1H), 4.26 (m, 4H), 2.36 (s, 3H), 1.48 (s, 9H), 1.37 (m, 6 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 71838-16-9.

Reference:
Patent; CENGENT THERAPEUTICS, INC.; WO2006/28970; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com