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