p-Chlorothiophenol → HCID 66986382, compound

Participants

Reaction Steps

To NaH (60% in mineral oil, 0.12 g, 3.0 mmol) in NMP (10 mL) was added 4-chlorobenzenethiol (0.44 g, 3.0 mmol). After stirring for 15 min, the reaction mixture was added to the product of Step 3 (1.09 g, 3.0 mmol) and CuBr (0.65 g, 4.5 mmol) in NMP (10 mL) under argon. The resulting mixture was kept at 140° C. for 4 h. After cooling, the reaction mixture was partitioned between H2O and EtOAc. The organic layer was separated, filtered through a thin pad of silica gel, and the filtrate was dried over anhydrous Na2SO4, and concentrated. The residue was purified by chromatography on silica gel (DCM to EtOAc) to give 4-[(4-chlorophenyl)thio]-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-imidazole. LCMS: [M+1]+=379.0

Provenance & Evidence