Water → HCID 18394850, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2'-O-benzyluridine [Wagner et al. (1974), J. Org. Chem. 39, 24-30] (334 mg 1 mM) carbon tetrabromide (500 mg) and DMF (4 ml) at 20° C. under Argon was added over 5 mins a solution of triphenylphosphine (340 mg) in DMF (2 ml). The mixture was stirred at 20° C. for 2 hrs, poured into water (60 ml) and extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried, and evaporated to an oil. This oil was chromatographed on 20 g of Merck silica gel (Art. 9385). Elution with 5% methanol in toluene gave 2'-O-benzyl-5'-bromo-5'-deoxyuridine (160 mg, 40%).

Provenance & Evidence