Hydrochloric Acid → 2,2-Difluoroethyl (4-methylphenyl)sulphonate

HRID 1776924Notes

Reaction equation

HRID 1776924 reaction equation
[F:1][CH:2]([F:5])[CH2:3][OH:4].[S:6](Cl)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7].Cl>C(Cl)Cl>[CH3:13][C:12]1[CH:14]=[CH:15][C:9]([S:6]([O:4][CH2:3][CH:2]([F:5])[F:1])(=[O:8])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 1361872,2-Difluoroethan-1-ol

Product 1

HCID 27823122,2-Difluoroethyl (4-methylphenyl)sulphonateYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 2,2-difluoroethanol (1 g, 12.2 mmol) in CH2Cl2 (15 mL) was added TsCl (3.5 g, 18.3 mmol) at 0° C. The mixture was stirred at room temperature overnight. Then aqueous HCl was added to the mixture to adjusted the mixture to pH<7 and the mixture was separated. The aqueous phase was extracted with EtOAc and the combined organic phases was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using column chromatography (petroleum ether:EtOAc=15:1) to provide 2,2-difluoroethyl 4-methylbenzenesulfonate. (2.5 g, yield: 86.8%). 1H-NMR (CDCl3, 400 MHz) δ 7.78 (d, J=8.0 Hz, 2H), 7.35 (d, J=8.0 Hz, 2H), 5.75˜6.04 (m, 1H), 4.10˜4.18 (m, 2H), 2.44 (s, 3H). MS (M+H)+: 267.

Workup

  1. customthe mixture was separated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic phases was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-b283f834a55545c69cbad02adf024a6c
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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