Hydrochloric Acid → N-(2,2,2-trifluoroethoxy)phthalimide

Participants

Reaction Steps

A dichloromethane (21 mL) solution of 3.9 mL of 2,2,2-trifluoroethanol and 4.3 mL of pyridine was added dropwise to a dichloromethane (83 mL) solution of 9.0 mL of trifluoromethanesulfonic anhydride under cooling with ice over a period of 25 minutes. Thereto was dropwise added a dichloromethane (60 mL) solution of 8.50 g of N-hydroxyphthalimide and 18.5 mL of N,N-diisopropylethylamine at the same temperature over a period of 45 minutes, which was then stirred for 22 hours. To the reaction mixture was added 100 mL of 1 mol/L hydrochloric acid. The organic layer was separated, washed sequentially with 1 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution, and then dried with anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=3:1) and washed with hexane to provide 4.43 g of N-(2,2,2-trifluoroethoxy)phthalimide as white solid form.

Provenance & Evidence