Methyl iodide → 1-Bromo-3-(2(S)-methoxy-3-phenylpropyl)benzene

Participants

Reaction Steps

To a solution of 1-(3-bromophenyl)-3-phenyl-2(S)-propanol (365 mg, 1.25 mmol) in 15 mL of anhydrous THF was added NaH (70% dispersion in mineral oil, 100 mg, 2.9 mmol, 2.3 equiv.) at 0° C. under N2. The mixture was warmed to room temperature and stirred for 30 min, then CH3I (1.75 g, 12.3 mmol, 9.8 equiv.) was added at room temperature. The mixture was stirred overnight at room temperature. The reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc (3×50 mL). The combined organic phases were washed with brine and dried over Na2SO4. After filtration and concentration, the residue was purified by CC on silica gel with EtOAc/petroleum ether 1:20 to provide the methyl ether (300 mg, 78%) as a yellow oil. LC-MS (ESI) m/z 306 (M+H+).

Provenance & Evidence