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

HRID 2374644Notes

Reaction equation

HRID 2374644 reaction equation
[F:1][C:2]([F:11])([C:7]([F:10])([F:9])[F:8])[CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].Cl>C(Cl)Cl>[F:1][C:2]([F:11])([C:7]([F:8])([F:9])[F:10])[CH2:3][CH2:4][CH2:5][O:6][S:20]([CH3:19])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

Product 1

HCID 120170564,4,5,5,5-Pentafluoropentyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  1. washWash the organic layer with HCl (0.5 N, 2×100 mL)
  2. dry with materialDry the organic layer (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customRecovered 11.48 g (96%) of the desired methanesulfonic acid 4,4,5,5,5-pentafluoro-pentylester as a light yellow oil

Sources & evidence

ORD record
ord-cf92ec8ddf9b45e1b66a217156b28248
Source dataset
uspto-grants-2008_12
Patent number
US07462647B2

Reaction notes

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