Hydrochloric Acid → 4,4,5,5,5-Pentafluoropentyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

Dissolve 4,4,5,5,5-pentafluoropentanol (8.27 g, 46.42 mmol) in CH2Cl2 (100 mL) and cooled the solution to 0° C. Add triethylamine (20.00 mL, 143.49 mmol), followed by the drop wise addition of methanesulfonyl chloride (4.40 mL, 56.84 mmol). Stir the solution for 45 minutes, then pour into HCl (0.5 N, 100 mL). Wash the organic layer with HCl (0.5 N, 2×100 mL). Dry the organic layer (Na2SO4), filter, and concentrate in vacuo. Recovered 11.48 g (96%) of the desired methanesulfonic acid 4,4,5,5,5-pentafluoro-pentylester as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 4.31 (t, J=6.0 Hz, 2H), 3.03 (s, 3H), 2.2 (m, 2H), 2.08 (m, 2H).

Provenance & Evidence