Synthetic Route of 444-29-1, A common heterocyclic compound, 444-29-1, name is 1-Iodo-2-(trifluoromethyl)benzene, molecular formula is C7H4F3I, 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: Synthesis of tert-butyl (Z)-(2-(4-(l-(4-(benzyloxy)phenyl)-2-(2- (trifluoromethyl)phenyl)but-l-en-l-yl)phenoxy)ethyl)carbamate 0 “C-RT/12 h Hi) l-iodo-2-(trifluoromethyl)benzene 4M KOH/80 °C/12 h To a stirred solution of l-(benzyloxy)-4-(but-l-yn-l-yl)benzene (2 g, 8.47 mmol, Example- 125, Step-4) in 2-methyl THF (20 mL), was added bis(pinacolato)diboron (2.15 g, 8.47 mmol), tetrakis(triphenylphosphine)platinum (0) (0.13 g, 0.104 mmol) under nitrogen atmosphere, reaction mixture was stirred at 90 °C for 12 h. The solution was allowed to cool to room temperature and tert-butyl (2-(4-iodophenoxy)ethyl)carbamate (2 g, 5.51 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.276 g, 0.393 mmol), cesium carbonate (5.1 g, 15.74 mmol) and 2-methyl THF (20 mL) were added. This mixture was degassed with nitrogen and water (0.2 mL) was added. This mixture was stirred at room temperature for 12 h. After completion of reaction, to the above reaction mixture 4M KOH (11 mL, 4.48 mmol) and l-iodo-2-(trifluoiOmethyl)benzene (3.2 g, 12.2 mmol) were added. Reaction mixture was stirred at 80 °C for 12 h. After completion of reaction, reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude material was purified by column chromatography over 230-400 mesh silica gel using 5percent EtOAc in n- hexane to afford tert-butyl (Z)-(2-(4-(l-(4-(benzyloxy)phenyl)-2-(2- (trifluoromethyl)phenyl)but-l-en-l-yl)phenoxy)ethyl)carbamate (2 g, 36percent).
The synthetic route of 444-29-1 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; HAO, Ming-Hong; KORPAL, Manav; NYAVANANDI, Vijay Kumar; PUYANG, Xiaoling; SAMAJDAR, Susanta; SMITH, Peter Gerard; WANG, John; ZHENG, Guo Zhu; ZHU, Ping; (161 pag.)WO2016/196342; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com