Benzyl Bromide → HCID 21106525, compound

Participants

Reaction Steps

4-Bromo-2H-phthalazin-1-one (10.38 g, 46 mmol) was dissolved in dimethylformamide (DMF) (60 ml). To this was added NaH (60%, 1.55 g, 46.2 mmol) as a DMF suspension (20 ml). The mixture was stirred at RT for 30 mins then benzyl bromide (13.82 g, 50.8 mmol) was added in one portion as a solution in DMF (20 ml). The reaction mixture was stirred for 2 hours then the DMF was removed under reduced pressure and the resulting crude material purified by column chromatography (gradient elution: 100% heptane to 20% EtOAc: heptane) to give the title compound (8.16 g, 56% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 8.30 (1H, dd), 8.03 (1H, ddd), 7.97-7.91 (2 H, m), 7.34-7.27 (5H, m), 5.31 (2H, s); MS (ESI+)=(M+H)+ 315 & 317

Provenance & Evidence