Electric Literature of 883502-14-5, A common heterocyclic compound, 883502-14-5, name is 1-Fluoro-2-iodo-3-methylbenzene, molecular formula is C7H6FI, 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 A: 2-Fluoro-6-methyl-benzonitrile: A 10 L round bottom flask equipped with adapter,thermocouple and stir bar was charged with DMA (6 L) and degassed under vacuum and purgedwith N2 three times. To the mixture was added Palladium Tetrakis triphenylphosphine (87.5 g,72.0 mmol) and the mixture was degassed under vacuum and purged with N2 three times. Thereaction was heated to 80 C for 30 min. 3-Fluoro-2-iodotoluene (575 g, 2.4 mol) and ZincCyanide (I7I.7 g, 1.46 mol) were added and the mixture was degassed under vacuum and purgedwith N2 three times. The reaction mixture was heated to 80 C for 16 h and then allowed to cooltoRT. The solution was added to a 2.0 L aqueous solution of IN NH40H and extracted three times with 1.5 L EtOAc. The extracts were washed with 2 L brine, dried over Na2S04, filteredand concentrated. The crude product was treated with mCPBA in cooled DCM and then purifiedby chromatography (PE/EA = IO:I) to get the title compound.
The synthetic route of 883502-14-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com