4-Toluenesulfonyl chloride → 2,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

HRID 1666874Notes

Reaction equation

HRID 1666874 reaction equation
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][OH:4].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[S:16]([C:13]1[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=1)([O:4][CH2:3][C:2]([F:9])([F:1])[C:5]([F:8])([F:7])[F:6])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 98722,2,3,3,3-Pentafluoropropanol

Product 1

HCID 27760172,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 2,2,3,3,3-pentafluoropropan-1-ol (9.7 ml) and pyridine. Cool to between 0° C. and 10° C. and add portion-wise the p-toluenesulfonylchloride (6.2 g) and stir with warming to room temperature. After 3 hours at room temperature, pour the reaction mixture into ice water and stir for 30 min to give a solid. Filter the solid, wash with water, and dry to give of the title compound.

Workup

  1. temperatureCool to between 0° C. and 10° C.
  2. stirringstir for 30 min
  3. customto give a solid
  4. filtrationFilter the solid
  5. washwash with water
  6. customdry

Sources & evidence

ORD record
ord-4b3558cb51a64cdf864f359686a3d423
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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