Benzyl Bromide → 4-(Benzyloxy)-3-bromophenol

Participants

Reaction Steps

To a mixture of MeOH (50 mL) and K2CO3 (49.36 g, 357 mmole) at r.t was dripped commercially available 2-bromobenzene-1,4-diol (15 g, 79 mmole) in MeOH (25 mL), followed by the syringe addition of benzyl bromide (14.93 g, 10.38 mL). The resulting mixture was refluxed for 8 hours. The reaction was cooled to RT and poured into saturated aqueous ammonium chloride (500 mL) and extracted with ethyl acetate (2×150). The combined organic phases were washed with aqueous NaHCO3 solution (2×150 mL), aqueous 1N HCl solution (2×150 mL), and brine (2×150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 10% Ethyl acetate/Hexane). ESLRMS m/z 280.9 (M+H).

Provenance & Evidence