Iodopentafluoroethane → HCID 131735938, compound

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (102.0 mL, 85.5 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (57.0 mL, 85.5 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then a solution of 3-(3-bromo-phenyl)-N-methoxy-N-methylacrylamide (7.7 g, 28.5 mmol, in diethyl ether 50.0 mL) prepared in Step 1 of Preparation 4 was slowly added thereto at −78° C. The reaction mixture was stirred at room temperature for 1 hour, quenched with distilled water, acidified by a 10% potassium hydrogen sulfate solution (pH=5), and then extracted with diethyl ether. 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=1/30) to give 8.0 g of the titled compound as a yellow liquid.

1. additionwas slowly added
2. customat −78° C
3. stirringThe reaction mixture was stirred at room temperature for 1 hour
4. customquenched with distilled water
5. extractionextracted with diethyl ether
6. washThe extract was washed with a saturated solution of sodium hydrogen carbonate
7. dry with materialdried on anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customto give a yellow liquid residue
10. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/30)

ORD record

ord-4e899c40f07846a3b80b4b8f5151f3d8

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376420B2