Hydrochloric Acid → HCID 12687359, compound

Participants

Reaction Steps

4-(4-Bromophenoxy)benzil (3.81 g, 0.01 mole), trimethylsilylacetylene (1.96 g, 0.02 mole), and dichlorobis(triphenylphosphine)palladium (0.30 g) in triethylamine (20 ml) were placed under a nitrogen atmosphere in a sealed flask and heated at 66°-68° C. for four hours. The cooled brown reaction mixture was poured into cold dilute hydrochloric acid to yield a brown oil which was extracted with methylene chloride. The methylene chloride solution was washed with dilute aqueous hydrochloric acid and water, dried over magnesium sulfate, and concentrated on a rotary evaporator to yield a brown gum (4.0 g). The gum was extracted with boiling cyclohexane (100 ml) (small amount remained insoluble) and the solution treated with charcoal, filtered, and concentrated to yield 4-[(4-[trimethylsilyl)ethynyl]phenoxy]benzil as an orange gum (3.4 g, 85% yield). MS, no M+, major fragment m/e 293 [+CO--C6H4 --O--C6H4 --C≡C--Si(CH3)3 ].

Provenance & Evidence