Sulfuric Acid → 2-Tert-butyl-4-fluorophenol

Participants

Reaction Steps

To a stirred solution of 4-fluorophenol (5.00 g, 45.0 mmol) and tert-butanol (4.67 g, 63.0 mmol) in dichloromethane (80 mL) was added conc. sulfuric acid (3.0 mL) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate. The organic layer was washed with water, neutralized with saturated sodium hydrogen carbonate, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 100:0 to 90:10 heptane/ethyl acetate) provided 2-tert-butyl-4-fluorophenol (2.54 g, 34%) as a pale green oil.

Provenance & Evidence