Iodine → 2-(Prop-2-yn-1-yl)naphthalene

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a suspension of Mg powder (5.3 mmol) and one piece of iodine in THF (4 ml) is added 2-bromonaphthalene (4.6 mmol) in THF (2 ml) at room temperature and the mixture is stirred at 85° C. for 0.5 h. Copper(I) bromide (0.32 mmol) is added at room temperature then methoxyallene (4.6 mmol) in THF (3 ml) is added at 0° C. and the mixture is stirred at room temperature for 2 h. The mixture is poured into saturated ammonium chloride, extracted with AcOEt. The organic layer is washed with brine, dried over sodium sulfate and concentrated. Chromatography on silica gel (n-hexane:AcOEt=20:1) gives the product in 18% yield. Rf=0.5 (n-hexane:AcOEt=10:1)

Herkunft & Nachweise