Phenylacetylene → 2-(4-Phenylethynylphenyl)benzthiazole

Participants

Reaction Conditions

Reaction Steps

To a solution containing 2-(4-bromophenyl)benzthiazole (43.5 g 0.15 mol) and phenylacetylene (20 g, 0.19 mol) in 0.8 L of triethylamine was added the catalyst system consisting of dichlorobis-(triphenylphosphine)palladiumII (1 g), triphenylphosphine (0.3 g) and cuprous iodide (0.1 g). The reaction mixture was refluxed under a nitrogen atmosphere for 19 h. After cooling to 25° C., the reaction mixture was filtered and the filtrate poured into 3 L of water. The resulting light gray solid was isolated by filtration and dried in an oven at 110° C. Recrystallization from heptane using activated charcoal gave 37 g (78.9%) of a white crystalline product: m.p. 172°-173° C.

Provenance & Evidence