Reaction #1960490

Reaction equation

DIAD

2,3-difluorophenol

1-octyn-3-ol

triphenylphosphine

→

1-(1-ethynylhexyloxy)-2,3-difluorobenzene

Solvents

MTBE

THF

THF

Conditions

Workup

1. 1
   Washwashed with water
2. 2
   ExtractionThe aqueous phase is extracted with MTBE
3. 3
   Washthe combined organic phases are washed with saturated sodium chloride solution
4. 4
   OtherThe solution is dried
5. 5
   Otherevaporated to dryness
6. 6
   OtherThe residue is purified by column chromatography (SiO2, 1-chlorobutane)

Procedure

2.4 g (0.33 mol) of 2,3-difluorophenol are initially introduced in 1.2 l of THF together with 50.0 ml (0.34 mol) of 1-octyn-3-ol and 94.1 g (0.36 mol) of triphenylphosphine, and a solution of 76.1 ml (0.39 mol) of DIAD in 100 ml of THF is added dropwise. After 19 h at RT, the batch is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with saturated sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, 1-chlorobutane), giving 1-(1-ethynylhexyloxy)-2,3-difluorobenzene as a colourless oil.

Source