Tetrabutylammonium Fluoride → HCID 68455108, compound

Participants

Reaction Steps

To a solution of (4-chloro-2-fluoro-3-iodobenzyloxy)(tert-butyl)dimethylsilane (6.64 g, 16.6 mmol) in THF (60 mL) was added tetrabutylammonium fluoride, 1.0 M in THF (19.9 mL, 19.9 mmol). The reaction solution was stirred at RT for 1 h. The volatile solvents were removed in vacuo. The residue was diluted with diethyl ether (150 mL), and then washed with saturated aqueous solution of sodium bicarbonate, and brine. The resulting organic solution was then dried over magnesium sulfate and concentrated under reduced pressure. Flash chromatography on silica gel (dichloromethane) gave (4-chloro-2-fluoro-3-iodophenyl)methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.16-7.32 (2H, m), 4.66 (2H, d, J=5.7 Hz), 1.90 (1H, t, J=6.0 Hz)

Provenance & Evidence