Phenylacetylene → 5-Nitro-2-phenylbenzofuran

Participants

Reaction Conditions

Reaction Steps

A solution of 2-iodo-4-nitrophenol (500 mg, 1.89 mmol), prolinol (573 mg, 5.66 mmol), palladium on carbon (60 mg, 0.06 mmol), triphenylphosphine (59.4 mg, 0.226 mmol) and copper iodide (22 mg, 0.113 mmol) in water (6 mL) was stirred for 1 h at room temperature. Ethynylbenzene (482 mg, 4.72 mmol) was slowly added, and the resulting mixture was heated at 80° C. for 3 h. After cooling, ethyl acetate was added, and the mixture was passed through a pad of Celite®. The filtrate was washed with water; the combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting material was purified by column chromatography eluting with ethyl acetate/hexanes 1:40 v/v to afford 134 mg (30%) of the title compound.

Provenance & Evidence