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

HRID 1765357Notes

Reaction equation

[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12]O)=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1.C[Si]([Br:22])(C)C.[Li+].[Br-]>C(#N)C>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][Br:22])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4-Bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.74 g, 2.5 mmol) in acetonitrile (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 acetonitrile (15 ml). The reaction mixture was heated to 80° C. for 24 hours, after which time the reaction mixture was cooled to room temperature and the solvent removed under vacuum. The resulting residue was purified by flash column chromatography (elution: 85% heptane, 15% ethyl acetate) to give the title compound (0.4 g, 44% yield) as a white solid.

Workup

temperatureafter which time the reaction mixture was cooled to room temperature
customthe solvent removed under vacuum
customThe resulting residue was purified by flash column chromatography (elution: 85% heptane, 15% ethyl acetate)

Sources & evidence

ORD record: ord-b2bbeb38d8de47759b5a2ffb2f2e7d69
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07226923B2

Reaction notes

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