4-Toluenesulfonyl chloride → 3,3,3-Trifluoroprop-1-yl toluene-4-sulphonate

HRID 1666875Notes

Reaction equation

HRID 1666875 reaction equation
[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][OH:5].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>N1C=CC=CC=1>[S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)([O:5][CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 1375123,3,3-Trifluoro-1-propanol

Product 1

HCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add 3,3,3-trifluoropropan-1-ol (618 ml) and pyridine (224 ml). Cool to between 0° C. and 10° C. and add portion-wise p-toluenesulfonylchloride (147 g). Allow to warm to ambient temperature and stir overnight. Add HCl 0.5N (1.6 L), extract with ethyl acetate, combine the organic layers, dry over MgSO4, filter, and evaporate to give the title compound.

Workup

  1. temperatureCool to between 0° C. and 10° C.
  2. extractionAdd HCl 0.5N (1.6 L), extract with ethyl acetate
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. customevaporate

Sources & evidence

ORD record
ord-30dd29d3a741427bb773ae55b08e771d
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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