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

HRID 1931103Notes

Reaction equation

HRID 1931103 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>C(Cl)Cl.N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:5][CH2:4][CH2:3][C:2]([F:7])([F:6])[F:1])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 2

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

Product 1

HCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonateYield 68%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3,3-trifluoropropan-1-ol (5.0 g, 43.8 mmol) in CH2Cl2 (25 mL) and pyridine (25 mL) was added 4-(dimethylamino)pyridine (0.27 g, 2.2 mmol) followed by p-toluenesulfonyl chloride (8.4 g, 43.8 mmol). The mixture was allowed to stir at ambient temperature for 72 h then was quenched with 5% aqueous HCl (20 mL). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×7 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by column chromatography (SiO2, 75% hexanes in EtOAc) afforded the title compound (8.0 g, 29.8 mmol, 68% yield). MS (DCI/NH3) m/z 286 (M+NH4)+.

Workup

  1. customthen was quenched with 5% aqueous HCl (20 mL)
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2 (3×7 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (SiO2, 75% hexanes in EtOAc)

Sources & evidence

ORD record
ord-92af2715d30949b6a4f97223997e53cc
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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