Ammonium Chloride → HCID 10798147, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred -78° C. solution in THF (200 mL) under argon of 2-[5-(4-fluorophenoxy)-2-furyl]-1,1-dibromoethene (23.1 g, 63.81 mmol), prepared as in step 2, was added n-butyl lithium (51.0 mL, 127.62 mmol, 2.5M in hexanes). The reaction was stirred for 0.5 hours at -78° C. Aqueous ammonium chloride was added to the cold reaction, the ice bath was removed and the reaction mixture allowed to warm to room temperature. The majority of THF was removed in vacuo. The resulting mixture was partitioned between water and ether. The combined ether layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (hexanes) to give 6.5 g (50%) of 2-[5-(4-fluorophenoxy)-2-furyl]-ethyne.

Provenance & Evidence