Acetic Acid → 3-(8-Acetoxy-9-bromononyl)-1-methylthymine

Participants

Reaction Steps

A mixture of 3-(8,9-dihydroxynonyl)-1-methylthymine (2.16 g, 7.6 mmol) and a 30% solution of hydrogen bromide in acetic acid (4.5 mL, 23 mmol ) was stirred for 1 hour. The reaction was added slowly to a beaker containing sodium bicarbonate (8.4 g, 0.1 mol), ice water (30 mL), and dichloromethane (30 mL). The layers were separated and the aqueous layer extracted with dichloromethane (2×60 mL). The combined organic layers were washed with water (30 mL), saturated aqueous salt solution (30 mL), and dried over sodium sulfate. The solvent was removed to yield 2.59 g (85% yield) 3-(8-acetoxy-9-bromononyl)-1-methylthymine (inventive compound no. 1908) as a thick, slightly orange oil.

Provenance & Evidence