Sodium Iodide → Iodomethyl 4-fluorobenzoate

Participants

Reaction Steps

To a solution of chloromethyl 4-fluorobenzoate (3.0g, 15.9 mmol) in 50 mL of dry acetone, NaI (4.8 g, 31.8 mmol) was added and the mixture was stirred overnight. The solvent was removed and Et2O (150 mL) was added to the solid residues and the mixture was stirred for 10 min. After filtration the filtrate was washed with 5% NaHSO3 (aq) (2×25 mL) followed by brine. The organic solution was concentrated by rotary evaporation and purified by silica gel chromatography to give a light yellow oil. Yield 3.7 g (85%). 1H NMR (300 MHz, CDCl3): δ 6.16 (s, 2H), 7.17 (m, 2H), 8.08 (m, 2H).

Provenance & Evidence