Hydrogen Bromide → 1-Bromo alpha-D glucose tetraacetate

Participants

Reaction Steps

Hydrobromic acid (30% in acetic acid, 11.85 ml, 55.4 mmol) was added to β-D-glucose pentaacetate (12.01 g, 30.8 mmol) at 0° C. After 10 minutes, the resulting solution was warmed to room temperature and stirred for 4 hours. The reaction mixture was slowly poured, with stirring, into ice water (250 ml) and was stirred until the product solidified. The product was collected by vacuum filtration and washed with cold water. The white solid was dissolved in carbon tetrachloride (60 ml) and washed with H2O (1×20 ml), saturated aqueous NaHCO3 (3×20 ml, until pH=7), H2O (1×20 ml), dried with CaCl2, and poured into cold petroleum ether (250 ml). After 30 min, the crystalline product was collected by vacuum filtration to give the target compound as a white solid (10.0 g, 80%).

Provenance & Evidence