Sodium Iodide → 5-bromobenzene-1,3-diol

Participants

Reaction Steps

To a suspension of 5-bromo-1,3-dimethoxy-benzene (15 g, 67.02 mmol) and sodium iodide (100.5 g, 670.2 mmol) in acetonitrile (577 mL) was added trimethylsilyl chloride (42.39 mL, 335.1 mmol) at room temperature. Then, the resulting light yellow suspension was heated to reflux for 48 h. Then, it was cooled to room temperature and diluted with water (150 mL). The organic compound was extracted into ethyl acetate (2×150 mL) and the combined ethyl acetate extracts were washed with saturated sodium thiosulfate solution (300 mL) to remove the iodine color and was also washed with brine solution (300 mL). Then, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by using an ISCO 330 g column, eluting with 5-30% ethyl acetate in hexanes to obtain 5-bromo-benzene-1,3-diol (9.24 g, 73%) as a light brown solid: ES(+)-HRMS m/e calcd for C6H5BrO2 (M+H)+ 189.2341. found 189.2346.

Provenance & Evidence