Iodopentafluoroethane → HCID 131735935, compound

Participants

Reaction Steps

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (17.1 mL, 14.3 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (9.6 mL, 14.3 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then a solution of 3-(5-bromo-pyridin-2-yl)-N-methoxy-N-methyl-acrylamide (1.3 g, 4.8 mmol, in tetrahydrofuran 12.0 mL) prepared in Step 2 was slowly added thereto at −78° C. The reaction mixture was stirred at room temperature for 2 hours, 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 0.9 g of the titled compound as a yellow liquid.

Provenance & Evidence