Iodopentafluoroethane → HCID 131735944, compound

Participants

Reaction Steps

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (42.1 mL, 35.3 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (23.6 mL, 35.3 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then a solution of 3-(6-bromo-pyridin-2-yl)-N-methoxy-N-methyl-acrylamide (3.2 g, 11.8 mmol, in tetrahydrofuran 30.0 mL) prepared in Step 2 was slowly added 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, 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 2.4 g of the titled compound as a yellow liquid.

Provenance & Evidence