Deoxyadenosine → 8-Bromo-2'-deoxyadenosine

Participants

Reaction Steps

2′-Deoxyadenosine (7 gm. 25.9 mmol) was dissolved in sodium acetate buffer (150, 1 M, pH5.0) by worming it to about 50 C, then was cooled dawn to 30 C, then 3 ml of bromine in 100 ml of the same buffer was added dropwise at RT for 15 min., to the reaction. After, 6 hrs the TLC on silica gel (20% MeOH in CH2Cl2) showed that all starting material was converted to a new product. The reaction was discolored by adding some sodium metabisulfite (Na2S2O5) while it was stirring, the color changed to a white solution, the pH of the reaction was neutralized by adding NaOH (1M solution). The reaction mixture was kept at 4° C. (refrigerator) for 16 hrs. Next day the solid material was filtered, washed with cold water, then acetone to give a solid yellow powder product (5.75 gm. 64%). The structure of this product was confirmed by H NMR and ES-MS.

Provenance & Evidence