These common heterocyclic compound, 202865-85-8, name is 1-Bromo-4-iodo-2-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. category: iodides-buliding-blocks
To a 2:1 (v/v) toluene: ethanol solution (0.034 M) of methyl 3-methyl-2 -(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yI)benzoate (1 eq.) from the previous step and 2- bromo-5-iodotoluene (1.2 eq.) was added was added trans-bis(triphenylphospliine) palladium(II) bromide (0.12 eq.). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, Na2C03 (2 M aq. solution, 3 eq.) was added and the resulting mixture was heated at 50 C for 12 h. The now black suspension was cooled to RT, diluted with ether and quenched with 10% aq. HC1. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were then washed further with 1 N aq. NaOH, water and brine, dried over Na2S04, filtered and the filtrate concentrated in vacuo. Purification of the crude product by way of flash chromatography (Si02, Hex -> 1 :1 (v/v) Hex: EtOAc) afforded the title compound as a colorless oil.
The synthetic route of 1-Bromo-4-iodo-2-methylbenzene has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK FROSST CANADA LTD.; CHEN, Austin; ASPIOTIS, Renee; MCKAY, Daniel; HAN, Yongxin; FOURNIER, Pierre-Andre; WO2011/57382; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com