Triethylamine → 2-Benzyloxy-4-bromomethyl-1-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (3-benzyloxy-4-nitrophenyl)-methanol (11.0 g, 0.042 mol) in anhydrous THF is added triethylamine (8.7 g, 0.86 mol). The mixture is cooled to −20° C., followed by the addition of methanesulfonyl chloride (5.8 g, 0.051 mol) and then stirred at −20° C. for 45 min. To this mixture is added lithium bromide (37.3 g, 0.43 mol) in anhydrous THF (40 mL) over 40 min. followed by stirring at ambient temperature for 2 h. The suspension is concentrated under reduced pressure and diluted with EtOAc and water. The organic phase is washed with brine, dried over MgSO4, filtered and concentrated to afford 2-benzyloxy-4-bromomethyl-1-nitrobenzene as a yellow solid.

Provenance & Evidence