Synthetic Route of 116632-39-4, 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. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Apparatus set-up: (0416) A 10 L 3 -necked round-bottomed flask, equipped with a mechanical overhead stirrer, reflux condenser, nitrogen inlet and exhaust. (0417) Experimental Procedure: (0418) Intermediate 3 (200 g, 0.644 mol) and intermediate 4 (190.9 g, 0.644 mol) were taken in 1, 2-dimethoxy ethane (2 L). (0419) Sodium carbonate solution (136.5 g, 1.288 mol, dissolved in 1 L of water) was added. (0420) The reaction mixture was degassed with nitrogen for an hour. (0421) Pd(PPh3)4 (7.44 g, 0.00644 mol) was added and heated at 100 C for 18 h. (0422) After completion of the reaction, it was filtered through a Florosil-silica plug and concentrated. (0423) The residue was dissolved in ethyl acetate (2 L), washed with water (1 L), brine (1 L), dried over sodium sulphate and concentrated. The crude product (200 g) was purified by silica column chromatography using hexane as an eluent to get 160 g of Intermediate D with 93 % HPLC purity. (0424) It was again purified by hot acetonitrile crystallization to get 135 g of Intermediate D with 97 % HPLC purity. (0425) It was further purified by hot acetonitrile crystallization to get 130 g of Intermediate D with 98.22 % HPLC purity. (0426) 130 g of Intermediate D at 98.22 % HPLC purity was crystallized with hot ethyl acetate/ methanol (1: 1.5) to get 100 g of Intermediate D with 98.9 % HPLC purity. (0427) 100 g of Intermediate D at 98.9 % HPLC purity was crystallized with hot ethyl acetate/ methanol (1: 1) to get 60 g of Intermediate D with 99.79 % HPLC purity. (0428) Filtrate obtained from all the above crystallizations were combined and concentrated to get 55 g at 97.2 % HPLC purity. (0429) 55 g of Intermediate D 97.2 % HPLC purity was crystallized with hot ethyl acetate/ methanol (1:0.8) to get 24 g of Intermediate D with 99.81 % HPLC purity. (0430) 24 g of Intermediate D at 99.81 % purity and 60 g of 99.79 % purity were combined, dissolved in dichloromethane (500 mL), heated to 45 C, filtered the hot solution and concentrated to get 80.5 g of Intermediate D with 99.70 % HPLC purity as white solid. (0431) ^-NMR (400 MHz, COCh): delta [ppm] 2.31 (s, 3H), 7.21 (d, / = 8.00 Hz, 1H), 7.40-7.45 (m, 2H), 7.48-7.52 (m, 3H), 7.89-7.91 (m, 2H), 8.07 (s, 1H), 8.15-8.17 (m, 1H).
The synthetic route of 5-Bromo-2-iodotoluene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL CO., LTD; HUMPHRIES, Martin; TARRAN, William; KAMTEKAR, Kiran; STACKHOUSE, Philip; LEE, James; (76 pag.)WO2017/153731; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com