Sodium Iodide → 4-Bromo-3-methyl-1-(2-propoxyethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

In DMF (120 ml) was dissolved 4-bromo-3-methylphenol (12 g). To the mixture were added potassium carbonate (11.5 g) and sodium iodide (9.6 g) and then added dropwise 2-chloroethylpropylether (9.7 ml), and the mixture was stirred at 90° C. for 10 hours and cooled to room temperature. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=12/1) to give 4-bromo-3-methyl-1-(2-propoxyethoxy)benzene (11.0 g). 1H-NMR (200 MHz, CDCl3) δ 0.93 (3H, t, J=7.2 Hz), 1.54-1.71 (2H, m), 2.25 (3H, s), 3.48 (2H, t, J=6.6 Hz), 3.73-3.79 (2H, m), 4.05-4.10 (2H, m), 6.63 (1H, dd, J=8.8, 2.8 Hz), 6.82 (1H, d, J=2.8 Hz), 7.38 (1H, d, J=8.8 Hz).

Provenance & Evidence