Pyridine → HCID 66891035, compound

Participants

Reaction Steps

A solution of {3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]phenyl}methanol (2.69 g, 10.26 mmol.) in dichloromethane (40 mL) was cooled to 0° C. followed by addition of pyridine (913 uL, 11.3 mmol.) then thionyl chloride (750 uL, 10.3 mmol.). The mixture was then allowed to warm to room temperature followed by addition of a second aliquot of pyridine (400 uL). After 5 minutes the organic solution was washed once with 0.1M aqueous hydrochloric acid then dried over anhydrous magnesium sulfate. Filtration and concentration afforded 5-(chloromethyl)-1-fluoro-2-(methyloxy)-3-[(phenylmethyl)oxy]benzene (2.88 g, 100% yield) as a clear oil that was used without further purification. GCMS for C15H14O2FCl: 280 (M+).

Provenance & Evidence