Iodopentafluoroethane → HCID 131735949, compound

Participants

Reaction Steps

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (31.6 mL, 26.6 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (17.7 mL, 26.6 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then a solution of 3-(4-bromo-pyridin-2-yl)-N-methoxy-N-methyl-acrylamide (2.4 g, 8.9 mmol, in diethyl ether/tetrahydrofuran 20.0 mL/20.0 mL) prepared in Step 2 solution was slowly added thereto at −78° C. The reaction mixture was stirred at −78° C. for 1 hour, quenched with distilled water at room temperature, 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=1/5) to give 2.2 g of the titled compound as a yellow solid.

Provenance & Evidence