beta-D-Glucose pentaacetate → alpha-D-Glucopyranosyl bromide, tetraacetate

Participants

Reaction Steps

β-D-Glucose pentaacetate (2.5 g, 6.41 mmol) was added to HBr-AcOH (30%) with shaking. The reaction mixture was stirred at room temperature for 2 hours. The resultant reaction mixture was diluted with CHCl3 (50 mL), and the mixture was poured into ice water (15 mL). The chloroform layer was separated into an aqueous layer and a chloroform extraction layer (2×20 mL of CHCl3). The chloroform extraction layer was combined with the chloroform layer, and the mixture was then washed with water and dried over MgSO4, to thereby obtain acetobromo-α-D-glucose (4). The solvent was removed under reduced pressure, and the residue was recrystallized from a mixed solution of AcOEt and n-hexane, to thereby obtain a colorless needles 4 (2.23 g, 85%).

Provenance & Evidence