Sodium Iodide → 4-Iodophenylsulfur Pentafluoride

Participants

Reaction Steps

NaI (22.0 mg, 0.147 mmol) was added portion-wise to a solution of 1 (31.0 mg, 0.0974 mmol) and anisole (96.0 mg, 0.888 mmol) in CH3CN (53.5 mg). The reaction mixture was neutralized with Na2CO3 and filtered through Celite 545 using hexane. The solvent was evaporated to give a pale yellow oil, Silica column chromatography with hexane afforded 25b (15.3 mg, 48%), 2-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (4.0 mg, 13%), 3-methoxy-4′-(pentafluorosulfanyl) biphenyl as a colorless oil (0.2 mg, 1%), a fraction containing both 3-methoxy-4′-(pentafluorosulfanyl)biphenyl and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl (1:1) as colorless oil (2.0 mg, 7%), and 4-methoxy-4′-(pentafluorosulfanyl)biphenyl as colorless crystals (0.7 mg, 2%).

Provenance & Evidence