Triethylamine → Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate

Participants

Reaction Steps

A solution of tert-butyl(2-bromo-4-chlorophenoxy)acetate (Intermediate 1; 19.40 g; 60.3 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) (2.65 g; 3.62 mmol) in THF (290 mL) was degassed during 2 minutes under nitrogen then triethylamine (12.5 mL; 91 mmol) and (trimethylsilyl)acetylene (Aldrich; 10.2 mL; 72.4 mmol) were added. The reaction mixture was stirred under nitrogen for 10 minutes before being treated with copper iodide (689 mg; 3.62 mmol) and triethlyamine (12.5 mL, 90.5 mmol) and stirred at 60° C. for 24 h. The reaction mixture was filtered through Celite and the cake of Celite was washed with EtOAc. The resulting filtrate was washed with HCl 1N and brine, dried over MgSO4, filtered and concentrated to dryness affording a dark brown sticky solid, which was suspended in petroleum ether (350 mL). The resulting precipitate was filtered, washed with petroleum ether (2×150 mL) and the filtrated was concentrated to dryness affording the crude product (17.7 g, 87%) as a brown oil.

Provenance & Evidence