Reaction #49798

Reaction equation

Catechol

potassium carbonate

2,4-difluoronitrobenzene

→

title product

Yield 55.0%

o-(5-Fluoro-2-nitrophenoxy)phenol

Yield 55.0%

Solvents

acetonitrile

brine

—

hexanes

methylene chloride

Conditions

Workup

1. 1
   Extractionextracted with ether
2. 2
   ExtractionThe organic extract
3. 3
   Washis washed with brine
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Otherto obtain a brown gum

Procedure

Catechol (103.8 g, 0.94 mol) and potassium carbonate (129.9 g, 0.94 mol) are added to a solution of 2,4-difluoronitrobenzene (50.0 g, 0.314 mol) in acetonitrile. The reaction mixture is stirred at 28° C. for 24 hours, poured into brine and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown gum. Flash chromatography of the gum using silica gel and a 10% hexanes in methylene chloride solution gives the title product as a yellow solid (43 g) which is identified by 1HNMR spectral analysis.

Source