p-Toluenesulfonic acid → 2-Fluoroethyl p-Toluenesulfonate

HRID 1046781Notes

Reaction equation

HRID 1046781 reaction equation
[F:1][CH2:2][CH2:3][OH:4].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8]([S:11](O)(=[O:13])=[O:12])=[CH:7][CH:6]=1>N1C=CC=CC=1>[F:1][CH2:2][CH2:3][O:4][S:11]([C:8]1[CH:9]=[CH:10][C:5]([CH3:15])=[CH:6][CH:7]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 97372-Fluoroethanol

Product 1

HCID 2560192-Fluoroethyl p-ToluenesulfonateYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1g (15.6 mmol) of 2-fluoroethanol was dissolved in pyridine (15 mL), and 6.5 g (34.1 mmol) of p-toluenesulfonic acid was added thereto over a period of 30 minutes while stirring on ice. The mixture was stirred at 0° C. under nitrogen atmosphere for 3 hours, and after adding 35 mL of ice water to the reaction mixture, extraction was performed with 30 mL of ethyl acetate. The obtained organic layer was washed three times with 30 mL of 1N hydrochloric acid, and then further washed with sodium carbonate solution and saturated saline. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure to yield the title compound (3.19 g, 94%) as a colorless oil.

Workup

  1. stirringThe mixture was stirred at 0° C. under nitrogen atmosphere for 3 hours
  2. extractionto the reaction mixture, extraction
  3. washThe obtained organic layer was washed three times with 30 mL of 1N hydrochloric acid
  4. washfurther washed with sodium carbonate solution and saturated saline
  5. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-59777da0c9ef4c26b668bab7d8943cc7
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

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