Introduction of a new synthetic route about 2-Bromo-1-iodo-4-methylbenzene

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.

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