Phenylacetylene → HCID 59992763, compound

Participants

Reaction Steps

5-Bromonaphthacene (1.00 g, 3.26 mmol, prepared as described in Example 1, Step 1), 31 mg of copper(I) iodide (0.163 mmol), 85 mg of triphenylphosphine (0.33 mmol) and 114 mg of dichlorobis(triphenylphosphine)palladium(II) catalyst (0.163 mmol) were added to an oven-dried glass pressure tube equipped with a magnetic stirrer. Dry triethylamine (20 ml) was added and the mixture was degassed with nitrogen for 15 minutes. Phenylacetylene (0.5 g, 0.46 ml, 4.88 mmol) was then added by syringe. The tube was sealed and heated in an oil bath to 95° C. while covered with aluminum foil to exclude light (for the duration of the reaction and work up, exposure to light was minimized). The reaction mixture was heated for two hours, and then allowed to cool slowly. The tube contents were dark red with a white precipitate. Upon further cooling, a dark red precipitate formed. TLC analysis with 30% dichloromethane/hexanes showed that all 5-bromonaphthacene had been consumed.

Provenance & Evidence