Boron tribromide → 5-bromobenzene-1,3-diol

Participants

Reaction Steps

To a solution of (35) (15.0 g, 69.0 mmol) in CH2Cl2 (40 mL), cooled to 0° C., a 1 M BBr3 solution in CH2Cl2 (140 mL, 140 mmol) was added dropwise. The ice bath was removed and the reaction was stirred at room temperature for 18 h. The reaction was quenched with MeOH and concentrated. The residue was dissolved in EtOAc (500 mL) and washed with water (300 mL). The organic layer was separated, dried (Na2SO4) and concentrated to give 5-bromobenzene-1,3-diol (45) (13.03 g, >99%) as an orange oil.

Provenance & Evidence