Iodopentafluoroethane → 1-(4-Bromo-phenyl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one

To a saturated solution of pentafluoroiodoethane (0.84 M, in diethyl ether) (198.3 mL, 166.6 mmol), was slowly added a solution of methyllithium/lithium bromide (1.5 M, in diethyl ether) (111.1 mL, 166.6 mmol) under nitrogen atmosphere at −78° C. The reaction mixture was stirred for 20 minutes and then a solution of 3-(4-bromo-phenyl)-N-methoxy-N-methyl-acrylamide (15.0 g, 55.5 mmol, in diethyl ether 20.0 mL) prepared in Step 1 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=1/60) to give 9.0 g of the titled compound as a yellow solid.

1. additionwas slowly added
2. customat −78° C
3. stirringThe reaction mixture was stirred at room temperature
4. customquenched with distilled water
5. extractionextracted with diethyl ether three times
6. extractionThe combined extract
7. washwas washed with a saturated solution of sodium hydrogen carbonate
8. dry with materialdried on anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customto give a yellow liquid residue
11. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/60)

ORD record

ord-844a062d0f1748f894d9cb0594c57836

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376420B2