Bromotrimethylsilane → 4-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.74 g, 2.5 mmol) in MeCN (5 ml) was added dropwise to a stirred suspension of trimethylsilyl bromide (TMSBr) (0.9 g, 6.3 mmol) and LiBr (0.41 g, 5 mmol) in MeCN (15 ml). The reaction mixture was heated to 80° C. for 24 hours, after which time the reaction mixture was cooled to RT and the solvent removed under vacuum. The resulting residue was purified by flash column chromatography (elution: 85% heptane, 15% EtOAc) to give the title compound (0.4 g, 44% yield) as a white solid. 1H-NMR: (250 MHz, D6- DMSO), 8.37 (1H, s), 8.03 (1H, d), 7.94 (1 H, d), 5.26-5.09 (1H, m), 4.93 (2H, s), 1.35 (6H, d).

Provenance & Evidence