4-Bromoanisole → HCID 18471813, compound

Participants

Reaction Steps

To a round-bottom flask equipped with a stirbar is added acetylene 4F (R=methyl) (2 g), 4-bromoanisole (3.40 g), palladium catalyst (made by mixing together 29.11 g triphenylphosphine, 3.28 g PdCl2, and 200 mL dipropylamine; refluxing the slurry for 3 hours to get a yellow slurry; cooling to room temperature; adding 3.69 g copper (II) acetate monohydrate; refluxing 1 hour; cooling and storing in the freezer) (330 mg), and diisopropylamine (80 mL). A stream of dry nitrogen is bubbled through this solution for 15 minutes to degas it, and the solution is then refluxed under a nitrogen atmosphere for 5 hours. The cooled solution is poured onto silica gel and eluted with 1:1 hexanes:ethyl acetate to give the product. The methyl group may be removed using the conditions used for deprotection of methyl ether 2F.

Provenance & Evidence