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

HRID 1371947Notes

Reaction equation

HRID 1371947 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 (61.8 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-8b683b9ed17041afb862a8ed35a00419
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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