Reaktion #44759

Reaktionsgleichung

2,2,3,3,3-pentafluoropropyl 4-methylbenzenesulfonate

4-hydroxybenzaldehyde

potassium carbonate

→

4-(2,2,3,3,3-pentafluoropropoxy)benzaldehyde

Ausbeute 30.2%

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   Temperaturheated at 100° C. for 7 h
4. 4
   Temperaturto cool
5. 5
   Waschenwashed with water (3×) and brine
6. 6
   Einengenconcentrated
7. 7
   SonstigePurification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane

Vorschrift

A solution of 4-hydroxybenzaldehyde (2 g, 16.7 mmol) in DMF (33 mL) was stirred as solid potassium carbonate (4.1 g, 29.7 mmol) was added, and the reaction mixture was then stirred at RT. After 30 min, solid 2,2,3,3,3-pentafluoropropyl 4-methylbenzenesulfonate (5 g, 16.4 mmol) was added into the reaction mixture. The mixture was stirred and heated at 100° C. for 7 h. The reaction mixture was allowed to cool, diluted with ethyl acetate, washed with water (3×) and brine, and concentrated. Purification by flash chromatography on silica gel using a gradient of ethyl acetate in hexane afforded 4-(2,2,3,3,3-pentafluoropropoxy)benzaldehyde (1.26 g).

Quelle