Iodopentafluoroethane → HCID 131735942, compound

Participants

Reaction Steps

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (15.3 mL, 13.3 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (8.9 mL, 13.3 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then 3-(5-bromo-2-fluoro-phenyl)-N-methoxy-N-methylacrylamide (1.3 g, 4.4 mmol, in tetrahydrofuran 10.0 mL) prepared in Step 3 was slowly added thereto at −78° C. The reaction mixture was stirred at room temperature, quenched with distilled water, acidified by a 10% potassium hydrogen sulfate solution (pH=5), and then extracted with ethyl acetate. The extract was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10) to give 620.0 mg of the titled compound as a yellow liquid.

Provenance & Evidence