Aniline → 3,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)aniline

Participants

Reaction Steps

To 1.1 liters of tetrahydrofuran containing 44.5 g of 2,6-dichloro-4-aminophenol and 3.2 g potassium hydroxide, was added subsurface 38.7 g of hexafluoropropene. The addition was complete in 25 minutes at a temperature of 8-11° C. Analysis by liquid chromatography indicates no starting aniline present. Most of the THF was removed under vacuum, 500 mL water was added and the resulting mixture was extracted 3×500 mL ethyl ether. The combined extracts were washed with 2×100 mL 1N NaOH, 2×200 mL brine, dried over anhydrous sodium sulfate, filtered and the solvent removed under vacuum to give a mixture. This mixture was separated by prep LC to give 46.8 g of 3,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)aniline and ~4 g of 3,5-dichloro-4-(1,2,3,3,3-pentafluoropropenoxy)aniline Proton and 19F nmr and mass spectra were consistent with the proposed structures.

Provenance & Evidence