4-Toluenesulfonyl chloride → HCID 86668139, compound

HRID 1027983Notes

Reaction equation

HRID 1027983 reaction equation
[F:1][CH2:2][CH:3]([OH:6])[CH2:4][F:5].[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]>N1C=CC=CC=1>[S:7]([O:6][CH:3]([CH2:4][F:5])[CH2:2][F:1])([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 679851,3-Difluoro-2-propanol

Product 1

HCID 86668139HCID 86668139, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,3-difluoro-2-propanol (60.75 g, 633 mmol) was dissolved in pyridine (375 mL) at 0° C. Tosyl chloride (134 g, 700 mmol) was added in portions and stirred overnight at room temperature. Pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate. The mixture was washed sequentially with dilute aqueous HCl, water, sat. aq. NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The residue was cooled to −78° C. until crystals began to form. The material was triturated with ice-cold hexane (2×200 mL) and filtered to provide O-Tosyl-1,3-difluoro-2-propanol as a white low-melting solid (143.9 g, 91%).

Workup

  1. customPyridine was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washThe mixture was washed sequentially with dilute aqueous HCl, water, sat. aq. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. temperatureThe residue was cooled to −78° C. until crystals
  8. customto form
  9. customThe material was triturated with ice-cold hexane (2×200 mL)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5384b04d23144ddbac07ebeb98ed4a4e
Source dataset
uspto-grants-2014_05
Patent number
US08735414B2

Reaction notes

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