Pyridine → 2,2,3,3,3-Pentafluoropropyl p-Toluenesulfonate

HRID 733287

Reaction equation

HRID 733287 reaction equation
[F:1][C:2]([F:9])([C:5]([F:8])([F:7])[F:6])[CH2:3][OH:4].N1C=CC=CC=1.[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[S:16]([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)([O:4][CH2:3][C:2]([F:9])([F:1])[C:5]([F:8])([F:7])[F:6])(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 98722,2,3,3,3-PentafluoropropanolHCID 11430Potassium Carbonate

Product 1

HCID 27760172,2,3,3,3-Pentafluoropropyl p-ToluenesulfonateYield 84%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2,2,3,3,3-pentafluoropropanol (5.0 mL, 50 mmol) and pyridine (8.1 mL, 100 mmol) in chloroform (100 mL), cooled at 0° C. and under argon, tosyl chloride (14.29 g, 75 mmol) was slowly added. The resulting mixture was allowed to warm up to room temperature and was stirred at this temperature overnight. Then, 10% aqueous K2CO3 solution was added and the mixture was vigorously stirred for 30 min. The layers were separated, and the organic layer was treated again with K2CO3. After that, it was washed with 2 N HCl, dried over Na2SO4 and the solvent was removed, yielding 12.72 g of the desired compound (84% yield).

Workup

  1. stirringthe mixture was vigorously stirred for 30 min
  2. customThe layers were separated
  3. additionthe organic layer was treated again with K2CO3
  4. washAfter that, it was washed with 2 N HCl
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-cca5ac87c6764be8ab6a7016fb72dc67
Source dataset
uspto-grants-2009_09
Patent number
US07589125B2

Linked notes

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