Reaction #426741

Reaction equation

water

2-fluoroethanol

p-toluenesulphonyl chloride

EtOAc

→

title compound

Yield 78.0%

2-Fluoroethyl-p-toluenesulphonate

Yield 78.0%

Solvents

pyridine

Conditions

Workup

1. 1
   Temperaturemaintaining the temperature below 5° C
2. 2
   workup.WAITat room temperature for 12 h
3. 3
   TemperatureThe reaction mixture was cooled to 0° C.
4. 4
   ExtractionThe organic extract
5. 5
   Washwas washed with water (30 ml), 1 M HCl (until aqueous extracts were acidic), 10% sodium carbonate (2×30 ml), brine (40 ml)
6. 6
   Dryingdried (Na2SO4)
7. 7
   OtherThe solvent was removed under reduced pressure

Procedure

To a stirred solution of 2-fluoroethanol (1.92 g, 29.97 mmol) in dry pyridine (15 ml) under an atmosphere of argon at 0° C. was added p-toluenesulphonyl chloride over 15 min, maintaining the temperature below 5° C. The reaction mixture was then stirred at 0° C. for 4 h, then at room temperature for 12 h. The reaction mixture was cooled to 0° C. and ice (15 g) was added followed by water (40 ml) and EtOAc (50 ml). The organic extract was washed with water (30 ml), 1 M HCl (until aqueous extracts were acidic), 10% sodium carbonate (2×30 ml), brine (40 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give the title compound (5.10 g, 78%) as a colourless oil.

Source