Iodopentafluoroethane → HCID 131735937, compound

Participants

Reaction Steps

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (200.9 mL, 168.8 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (112.5 mL, 168.8 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then a solution of N-methoxy-N-methyl-3-(4′-methylsulfanyl-biphenyl-3-yl)-acrylamide (17.6 g, 56.3 mmol, in tetrahydrofuran 20.0 mL) prepared in Step 2 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 diethyl ether three times. The combined 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=1/30) to give 16.4 g of the titled compound as a yellow solid.

Provenance & Evidence