Thionyl Chloride → 4-(Chloromethyl)-2-fluoro-1-methylbenzene

Participants

Reaction Steps

Thionyl chloride (0.892 g, 7.5 mmol) was added to a solution of the product of STEP 1 (1.0 g, 6.4 mmol) dropwise at 0° C. After 30 min, the reaction was quenched with crushed ice carefully, and diluted with H2O. The product was extracted with ether. The organic layer washed with saturated NaHCO3, brine and dried with Na0.2SO4. Ether was evaporated and the residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9) to give a clear liquid in 10.5 g. NMR spectra of the product were consistent for the proposed structure.

Provenance & Evidence