4-Toluenesulfonyl chloride → 2-Fluoroethyl p-Toluenesulfonate

HRID 599191

Reaction equation

HRID 599191 reaction equation
[F:1][CH2:2][CH2:3][OH:4].[S:5](Cl)([C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1)(=[O:7])=[O:6]>N1C=CC=CC=1>[CH3:12][C:11]1[CH:13]=[CH:14][C:8]([S:5]([O:4][CH2:3][CH2:2][F:1])(=[O:7])=[O:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 97372-Fluoroethanol

Product 1

HCID 2560192-Fluoroethyl p-ToluenesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 2-fluoroethanol (1.0 g, 15.6 mmol) in pyridine (15 mL) was added tosyl chloride (6.5 g, 34.1 mmol) over 30 min. The reaction mixture was stirred at 0° C. for 4 h and quenched by adding ice-cold water and EtOAc. The layers separated and the organic layer was washed successively with water, 1M HCl (5×), saturated Na2CO3 and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel (12 g) using 5% to 40% EtOAc in hexane as the eluant to obtain fluorotosylate 20 (3.2 g, 95%) as a slightly yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=10.0 Hz, 1H), 7.38 (d, J=10.0 Hz, 2H), 4.59 (dt, J=50.0 & 5.0 Hz, 2H), 4.28 (dt, J=30.0 & 5.0 Hz, 2H), 2.47 (s, 3H).

Workup

  1. customquenched
  2. additionby adding ice-cold water and EtOAc
  3. customThe layers separated
  4. washthe organic layer was washed successively with water, 1M HCl (5×), saturated Na2CO3 and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on silica gel (12 g)

Sources & evidence

ORD record
ord-560ca48835c6429fb0777279549ea3de
Source dataset
uspto-grants-2011_03
Patent number
US07897769B2

Linked notes

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