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0 °C

To a suspension of zirconium tetrachloride (1.17 g, 5 mmol) in DCM (10 ml) was added tert-butyl methyl ether (0.44 g, 5 mmol) at 0° C. After stirring for 30 minutes at 0° C., 3,5-difluorophenol (0.65 g, 5 mmol) in DCM was placed there and the mixture was stirred for 8 hours at 60° C. The reaction was quenched with saturated sodiumbicarbonate aqueous solution followed by addition of DCM. Then, organic layer was separated, dried over magnesium sulfate, evaporated in vacuo to give the residue which was purified through silica gel column chromatography eluting with hexane/EtOAc (20:1 to 4:1) to furnish 4-tert-butyl-3,5-difluorophenol as colorless oil (293 mg, 31%). 1H NMR (300 MHz, CDCl3): δ 1.42 (9H, t, J=2.2 Hz), 5.22 (1H, bs), 6.32 (2H, d, J=11.9 Hz).

1. stirringthe mixture was stirred for 8 hours at 60° C
2. customThe reaction was quenched with saturated sodiumbicarbonate aqueous solution
3. additionfollowed by addition of DCM
4. customThen, organic layer was separated
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customto give the residue which
8. customwas purified through silica gel column chromatography
9. washeluting with hexane/EtOAc (20:1 to 4:1)