Reaction #426696

Reaction equation

DIAD

2-fluoroethanol

4-hydroxybenzaldehyde

triphenylphosphine

→

4-(2-Fluoroethoxy)benzaldehyde

Yield 40.3%

title compound

Yield 40.3%

Solvents

THF

Conditions

Workup

1. 1
   Otherto rise to room temperature
2. 2
   workup.STIRRINGstirred for 48 h
3. 3
   OtherThe solvent was removed under reduced pressure
4. 4
   Otherthe residue was purified by flash chromatography (5:1 DCM/Hexane)

Procedure

To a mixture of 4-hydroxybenzaldehyde (1.45 g, 11.9 mmol), triphenylphosphine (6.87 g, 26.2 mmol) and 2-fluoroethanol (1.68 g, 26.2 mmol) in dry THF (70 ml) at 0° C., was added DIAD (5.29 g, 26.2 mmol) dropwise. The reaction mixture was stirred at 0° C. for 1 h then allowed to rise to room temperature and stirred for 48 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (5:1 DCM/Hexane) to give the title compound (0.807 g, 40%) as a colourless solid.

Source