Water → 3,3,3-Trifluoroprop-1-yl toluene-4-sulphonate

HRID 386919Notes

Reaction equation

HRID 386919 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(N(CC)CC)C.O>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[CH2:3][CH2:4][O:5][S:14]([C:11]1[CH:12]=[CH:13][C:8]([CH3:18])=[CH:9][CH:10]=1)(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1375123,3,3-Trifluoro-1-propanol

Product 1

HCID 126353403,3,3-Trifluoroprop-1-yl toluene-4-sulphonateYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3,3-trifluoro-propan-1-ol (1.1 g, 10.0 mmol) in DCM (10 mL) are added p-toluenesulfonyl chloride (2.3 g, 12.0 mmol), N,N-dimethylaminopyridine (0.1 g, 1.0 mmol) and triethyl amine (2.8 mL, 20.0 mmol). The reaction is stirred at room temperature for 3 d, then poured into water and extracted with DCM. The combined organic extracts are washed with 1N aqueous HCl solution, saturated aqueous NaHCO3 solution, brine and dried over Na2SO4, filtered and concentrated to afford 2.34 g of title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.47 (3H, s), 2.47-2.6 (2H, m), 4.22 (2H, t, J=6.4 Hz), 7.36 (2H, d, J=8.08 Hz), 7.8 (2H, d, J=7.8 Hz)

Workup

  1. extractionextracted with DCM
  2. washThe combined organic extracts are washed with 1N aqueous HCl solution, saturated aqueous NaHCO3 solution, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-617b47a64fa542f3b3d84d4e1b2ce796
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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