Triethylamine → 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyl trifluoromethanesulfonate

HRID 1105889Notes

Reaction equation

HRID 1105889 reaction equation
[F:1][C:2]([F:24])([C:20]([F:23])([F:22])[F:21])[C:3]([F:19])([F:18])[C:4]([F:17])([F:16])[C:5]([F:15])([F:14])[C:6]([F:13])([F:12])[C:7]([CH2:10][OH:11])([F:9])[F:8].C(N(CC)CC)C.[F:32][C:33]([F:39])([F:38])[S:34](Cl)(=[O:36])=[O:35]>C(Cl)Cl>[F:1][C:2]([F:24])([C:20]([F:21])([F:22])[F:23])[C:3]([F:18])([F:19])[C:4]([F:16])([F:17])[C:5]([F:15])([F:14])[C:6]([F:13])([F:12])[C:7]([CH2:10][O:11][S:34]([C:33]([F:39])([F:38])[F:32])(=[O:36])=[O:35])([F:9])[F:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67543(Perfluoroheptyl)methanolHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 110169092,2,3,3,4,4,5,5,6,6,7,7,8,8,8-Pentadecafluorooctyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 40 g of (pentadecafluoroheptyl)methanol, 11 g. of triethylamine, and 200 ml. of methylene chloride is stirred at -20° C. while a solution of 18 g. of trifluoromethanesulfonyl chloride in 50 ml. of methylene chloride is added. The solution is stirred for one hour at room temperature and then washed with ice-cold 10% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and water; dried over anhydrous magnesium sulfate; and evaporated. The residual brown liquid is distilled to yield the product as a colorless liquid.

Workup

  1. washwashed with ice-cold 10% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customand evaporated
  4. distillationThe residual brown liquid is distilled

Sources & evidence

ORD record
ord-20adc30c23ac48a19a467924b9f87be4
Source dataset
uspto-grants-1982_01
Patent number
US04310545

Reaction notes

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