Reaction #493944

Reaction equation

water

2-fluoroethanol

triethylamine

(CF3SO2)2O

→

2-fluoroethyl trifluoromethanesulfonate

Yield 82.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   WashThe organic layer was washed with satd aq NaHCO3 (100 mL) and brine (100 mL)
2. 2
   Otherdried
3. 3
   Concentrationconcentrated

Procedure

To a solution of 2-fluoroethanol (3.2 g, 50 mmol) and triethylamine (5.5 g, 55 mmol) in dichloromethane (60 mL) was added dropwise (CF3SO2)2O (15.5 g, 55 mmol) at −78° C. under N2. The mixture was stirred at 1020° C. for 1 h, and treated with water (100 mL). The organic layer was washed with satd aq NaHCO3 (100 mL) and brine (100 mL), dried, and concentrated to give 2-fluoroethyl trifluoromethanesulfonate (8 g, yield 82%).

Source