Reaktion #3117

Reaktionsgleichung

3,4-Dihydroxybenzaldehyde

methyl chlorodifluoroacetate

potassium carbonate

→

title compound

Ausbeute 38.0%

4-difluoromethoxy-3-hydroxybenzaldehyde

Ausbeute 38.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDMF was removed in vacuo
2. 2
   ExtraktionThe aqueous layer was extracted three times with ether
3. 3
   WaschenThe combined organic extracts were washed with water, with brine
4. 4
   Trocknenwere dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

Vorschrift

3,4-Dihydroxybenzaldehyde (0.50 g, 3.62 mmol, Aldrich), methyl chlorodifluoroacetate (0.52 g, 3.62 mmol, Aldrich) and potassium carbonate (0.50 g, 3.62 mmol) were combined in DMF (5.0 mL) under an argon atmosphere. After stirring at 60°-65° C. for 3 h, DMF was removed in vacuo and the residue was partioned between aqueous 3N HCl and ether. The aqueous layer was extracted three times with ether. The combined organic extracts were washed with water, with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide the title compound as a white solid (0.20 g, 38%). mp 83°-85° C.

Quelle