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

HRID 1765357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765357
[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

Komponenten

5

Edukt 3

HCID 76113BromotrimethylsilaneHCID 82050Lithium BromideHCID 21106569HCID 21106569, Verbindung

Produkt 1

HCID 211065684-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-oneAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b2bbeb38d8de47759b5a2ffb2f2e7d69
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226923B2

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