Reaction #3117

Reaction equation

3,4-Dihydroxybenzaldehyde

methyl chlorodifluoroacetate

potassium carbonate

→

title compound

Yield 38.0%

4-difluoromethoxy-3-hydroxybenzaldehyde

Yield 38.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherDMF was removed in vacuo
2. 2
   ExtractionThe aqueous layer was extracted three times with ether
3. 3
   WashThe combined organic extracts were washed with water, with brine
4. 4
   Dryingwere dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   OtherThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)

Procedure

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.

Source