Water → 4-Bromo-1-(methoxymethyl)-2-(methylsulfonyl)benzene

Participants

Reaction Steps

To a solution of (4-bromo-2-methanesulfonyl-phenyl)-methanol (preparation 112) (500 mg, 1.89 mmol) in DMF (10 mL) was added NaH (226 mg, 5.66 mmol, 60% in oil) at room temperature. After stirring at room temperature for 30 minutes, to above mixture was added MeI (230 mg, 10 mmol) at room temperature. The resulting mixture was stirred at room temperature for 3 hrs. TLC (petroleum ether:EtOAc 1:1) showed the reaction was complete. Then the mixture was poured into H2O (10 mL) and extracted with EtOAc (50 mL×3), washed with brine (10 mL×3), dried over sodium sulfate, concentrated in vacuo to give the residue, which was purified by a Biotage silica gel cartridge (petroleum ether/EtOAc 1:1, Rf˜0.5) to give the title compound (200 mg, 40%) as yellow oil.

Provenance & Evidence