4-Fluorophenol → HCID 53975395, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 960 mg (40 mmol) of sodium hydride in 50 mL of dimethyl sulfoxide is added 4.48 g (40 mmol) of 4-fluorophenol. The mixture is stirred until hydrogen evolution has ceased and then 4.10 g (40 mmol, 4.24 mL) of 5-chloro-1-pentyne is added. The mixture is heated to 65° C. for 1 hour, is diluted with water and is extracted with hexane. The hexane extract is washed with 2.5M aqueous sodium hydroxide and saturated brine and is dried over magnesium sulfate. The dried solution is filtered and rotoevaporated to give 7.1 g (99%) of title compound. IR: (film) 3310, 1508 cm-1 ; 1H NMR (CDCl3): δ1.97 (1H, t, J=3 Hz), 1.99 (2H, p, J=6 Hz), 2.40 (2H, dt, J=3, 7 Hz), 4.03 (2H, t, J=6 Hz), 6.84 (2H, m) and 6.96 (2H, t, J=8 Hz).

Provenance & Evidence